3-肼基-4-甲基苯甲酸盐酸盐 → 3-[5-Amino-4-(3-iodobenzoyl)-pyrazol-1-yl]-4-methylbenzoic acid

HRID 251334

反应方程式

HRID 251334 反应方程式
Cl.[NH:2]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:7]([OH:9])=[O:8])[NH2:3].[I:14][C:15]1[CH:16]=[C:17]([CH:31]=[CH:32][CH:33]=1)[C:18]([C:20](=[CH:23]NC1C=CC=CC=1)[C:21]#[N:22])=[O:19]>C(O)C.CO>[NH2:22][C:21]1[N:2]([C:4]2[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=2[CH3:13])[C:7]([OH:9])=[O:8])[N:3]=[CH:23][C:20]=1[C:18](=[O:19])[C:17]1[CH:31]=[CH:32][CH:33]=[C:15]([I:14])[CH:16]=1

参与物

5

反应物 2

HCID 567775083-肼基-4-甲基苯甲酸盐酸盐HCID 670242742-(3-Iodobenzoyl)-3-phenylaminoacrylonitrile

产物 1

HCID 111550723-[5-Amino-4-(3-iodobenzoyl)-pyrazol-1-yl]-4-methylbenzoic acid收率 22%

试剂、催化剂与溶剂 2

HCID 702乙醇溶剂HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂

反应条件

温度
75 °C

实验过程

To a stirred solution of 3-hydrazino-4-methyl-benzoic acid hydrochloride 1 (Example 3A, 314 mg, 1.54 mmol, 1.0 eq) in 50 mL of ethanol and 5 mL of methanol was added 2-(3-iodo-benzoyl)-3-phenylamino-acrylonitrile 2 (579 mg, 1.54 mmol, preparation: International Patent Application Publication No. WO 02/57101 A1, pg. 84). The mixture was heated to 75° C. for 18 h. The precipitated solids were collected on a fritted filter and were washed with ethanol to provide 3-[5-Amino-4-(3-iodo-benzoyl)-pyrazol-1-yl]-4-methyl-benzoic acid 3 (153 mg, 22%) as a white solid. MS m/z 448 [M+H]+; 1H NMR (300 MHz, DMSO-d6)<2.18 (s, 3H), 7.05 (bs, 2H), 7.34 (dd, J1=J2=7.7 Hz), 7.58 (d, J=8.1 Hz, 1H), 7.78 (s, 1H), 7.81 (m, 2H), 7.94 (m, 1H), 7.98 (m, 1H), 8.03 (m, 1H) ppm.

后处理

  1. custom579 mg, 1.54 mmol, preparation
  2. customThe precipitated solids were collected on a fritted filter
  3. washwere washed with ethanol

来源与证据

ORD记录
ord-6802a9aa694444c7a5eedb567fdd6746
来源数据集
uspto-grants-2011_01
专利号
US07863314B2

关联笔记

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