一种吲唑类化合物及其制备方法和应用_4

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H), L 67 (q, J = 7. 2Hz, 2H), 0. 93 (t, J = 7. 2Hz, 3H). ESI-MS: 478. 1 (M+Na)+.
[0126] 1-21 :固体;111.口.101-103。〇.1!1匪1?(6001抱,0)(:13)3 8.04(8,1!1),8.01(8,1!1),5· 12-5. 07 (m, 1H), 4. 13 (s, 2H), 2. 76 (t, J = 6. OHz, 2H), 2. 54 (t, J = 6. OHz, 2H), 1. 85 (q, J = 6. OHz, 4H), L 26 (d, J = 6. OHz, 6H). ESI-MS: 478. 1 (M+Na)+.
[0127] 1-22 :固体;m. p. 127-129 °C · 4 NMR(600MHz,CDC13) δ 8. 04(s,1H),8. 02(s,1H) ,4. 01 (s, 3H), 2. 75 (d, J = 6. OHz, 2H), 2. 55 (d, J = 6. OHz, 2H), 1. 86 (q, J = 6. OHz, 4H). ESI-MS :413. 9 (M+H)+.
[0128] 1-23:固体;m.p. 133-135 °C . NMR (6 0 0MHz, CDC13) δ 8. 04 (s, 1H), 8. 00 (s, 1H), 4. 78 (q, J = 7. 2Hz, 2H), 2. 74 (d, J = 6. OHz, 2H), 2. 54 (d, J = 6. OHz, 2H), L 85 (q, J = 6. OHz, 4H), L 42 (t, J = 7. 2Hz, 3H). ESI-MS: 428. 1 (M+H)+.
[0129] 1-24 :固体;m. p. 133-135 °C · 4 NMR (600MHz, DMS0-d6) δ 7. 90 (s, 1H),7. 88 (s, 1H ),4. 18 (s, 2H), 3. 80 (s, 3H), 2. 76 (t, J = 9. OHz, 2H), 2. 55 (t, J = 9. OHz, 2H), 1. 85 (q, J = 9. OHz, 4H). ESI-MS: 450. 1 (M+Na)+.
[0130] 1-25 :固体;m.p.113-115 °C . NMR (600MHz, DMS〇-d 6) δ 7. 90 (s, 1H), 7. 88 (s, 1H), 4. 72 (q, J = 7. 2Hz, 1H), 3. 77 (s, 3H), 2. 74 (t, J = 6. OHz, 2H), 2. 54(t, J = 6. OHz, 2H), 1. 85 (q, J = 6. OHz, 4H), L 72 (d, J = 7. 3Hz, 3H). ESI-MS :442. 1(M+H)+.
[0131] 1-26 :固体;m.p.141-143 °C . NMR (600MHz, DMS〇-d 6) δ 7. 90 (s, 1H), 7. 88 (s, 1H), 4. 15 (d, J = 3. 6Hz, 2H), 2. 75 (t, J = 9. OHz, 2H), 2. 54 (t, J = 9. OHz, 2H), 2. 32 (d, J = 3. 6Hz, 1H) 1. 85 (q, J = 6. OHz, 4H). ESI-MS: 394. 1 (M+H)+.
[0132] 1-27 :固体;m. p. 105-106 °C ·虫 NMR (600MHz, CDC13) δ 7. 88 (s, 1H),7. 87 (s ,1H), 6. 00(m, 1H), 5. 39(d, J = 12. OHz, 1H), 5. 21 (d, J = 12. OHz, 1H), 4. 00 (d, J = 6. 6Hz, 2H), 2. 74(t, J = 6. OHz, 2H), 2. 54 (t, J = 6. OHz, 2H), L 84 (q, J = 6. OHz, 4H). ESI-MS: 418. 1 (M+Na)+.
[0133] 实施例3
[0134] 本实施例用于说明本发明的吲唑类化合物的制备方法
[0135] 按照实施例1中的方法进行,不同的是在步骤1中将2, 4-二氟苯胺替换为 2-溴-4-氟苯胺,得到表1中所示的目标化合物1-28~1-40。
[0136] 化合物1-28~1-40确证数据如下:
[0137] 1-28:固 体;m.p. 108-110 °C . NMR (6 0 0MHz, CDC13) δ 8. 07 (s, 1H), 7. 85 (s, 1H), 4. 24 (q, J = 7. 2Hz, 2H), 4. 16 (s, 2H), 2. 75 (s, 2H), 2. 54 (s, 2H) ,L 85 (q, J = 6. 0Hz, 4H), L 29 (t, J = 7. 2Hz, 3H). ESI-MS: 486. 2 (M+H)+.
[0138] 1-29:固体;m.p. 108-109 °C . NMR (6 0 0MHz, CDC13) δ 8. 05(s, 1H), 7. 86(s, 1H), 4. 18(q, J = 7. 2Hz, 2H), 3. 61 (t, J = 7. 2Hz, 2H), 2. 91 (t, J =7. 2Hz, 2H) , 2. 74 (t, J = 6. 0Hz, 2H), 2. 54 (t, J = 6. 0Hz, 2H), 1. 85 (q, J = 6. 0Hz, 4H), L 27 (t, J = 7. 2Hz, 3H). ESI-MS: 522. 1 (M+Na)+.
[0139] 1-30 ::油状· 4 匪R(600MHz, CDC13) δ 8. 05(s, 1H), 7. 85(s, 1H), 4. 15(q, J =7. 2Hz, 2H), 3. 42 (t, J = 7. 2Hz, 2H) , 2. 76 (t, J = 6. 0Hz, 2H), 2. 54 (t, J = 6. 0Hz, 2H) , 2. 50 (t, J = 7. 2Hz, 2H) , 2. 17 (p, J = 7. 2Hz, 2H) , 1. 85 (q, J = 6. 0Hz, 4H), L 26 (t, J = 7. 2Hz, 3H). ESI-MS: 436. 1 (M+Na)+.
[0140] 1-31:固 体;m.p. 114-116 °C . NMR (6 0 0MHz, CDC13) δ 8. 06 (s, 1H), 7. 85 (s, 1H), 4. 69 (q, J = 7. 2Hz, 1H), 4. 22 (q, J = 7. 2Hz, 2H), 2. 74 (t, J =6. 0Hz, 2H), 2. 54 (t, J = 6. 0Hz, 2H), 1. 83 (q, J = 9. OHz, 4H), 1. 26 (t, J = 7. 2Hz, 3H). ESI-MS :500. 2 (M+H)+.
[0141] 1-32:固体;m.p. 128-130 °C . NMR (6 0 0MHz, CDC13) δ 8. 08(s, 1H), 7. 89(s, 1H), 4. 19(q, J = 7. 2Hz, 2H), 2. 74 (t, J = 6. OHz, 2H), 2. 54 (t, J =6. OHz, 2H), 1. 85 (q, J = 6. OHz, 4H), 1. 77 (s, 6H), 1. 20 (t, J = 7.2Hz,3H). ESI-MS: 514. 2 (M+H)+.
[0142] 1-33 :固体;m. p. 81-82°C · iNMR^OOMHz,CDC13) δ 8. 07(s, 1H), 7. 85(s, 1H), 4. 17 (s, 2H), 4. 14 (t, J = 6. 6Hz, 2H), 2. 76 (t, J = 6. OHz, 2H), 2. 55 (t, J = 6. OHz, 2H), 1. 85 (q, J =6. OHz, 4H), L 67 (q, J = 7. 2Hz, 2H), 0. 93 (t, J = 7. 2Hz, 3H). ESI-MS: 500. 2 (M+H)+.
[0143] 1-34 :固体;111.口.104-105。〇.1!1匪1?(6001抱,0)(:13)3 8.07(8,1!1),7.83(8,1!1),5· 06-5. 11 (m, 1H), 4. 12 (s, 2H), 2. 74 (t, J = 6. OHz, 2H), 2. 54 (t, J = 6. OHz, 2H), L 85 (q, J = 6. OHz, 4H), L 26 (d, J = 6. OHz, 6H). ESI-MS: 522. 0 (M+Na)+.
[0144] 1-35 :固体;m. p. 138-140 °C · 4 NMR(600MHz,CDC13) δ 8. 22(s,1H),8. 00(s,1H) ,4. 02 (s, 3H), 2. 74 (d, J = 6. OHz, 2H), 2. 54 (d, J = 6. OHz, 2H), 1. 85 (q, J = 6. OHz, 4H). ESI-MS: 477. 1 (M+Na)+.
[0145] 1-36:固体;m.p. 147-148 °C . NMR (6 0 0MHz, CDC13) δ 8. 21 (s, 1H), 7. 99 (s, 1H), 4. 48 (q, J = 7. 2Hz, 2H), 2. 74 (d, J = 6. OHz, 2H), 2. 54 (d, J = 6. OHz, 2H), L 85 (q, J = 6. OHz, 4H), L 42 (t, J = 7. 2Hz, 3H). ESI-MS: 472. 1 (M+H)+.
[0146] 1-37 :固体;m. p. 96-97 °C · 4 NMR(600MHz, DMS0-d6) δ 8. 07 (s, 1H), 7. 88 (s, 1H) ,4. 18 (s, 2H), 3. 79 (s, 3H), 2. 74 (t, J = 9. OHz, 2H), 2. 54 (t, J = 9. OHz, 2H), 1. 85 (q, J = 9. OHz, 4H). ESI-MS: 472. 1 (M+H)+.
[0147] 1-38 :固体;m. p. 1 38- 1 39 °C NM R ( 6 Ο Ο Μ H z , D M S 0 - d 6) δ 8. 07 (s, 1H), 7. 87 (s, 1H), 4. 72 (q, J = 7. 2Hz, 1H), 3. 77 (s, 3H), 2. 76 (t, J = 6. OHz, 2H), 2. 55(t, J = 6. OHz, 2H), 1. 80 (q, J = 6. OHz, 4H),
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