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Diisopropylethylamine → N-[1-(2-methoxyethyl)pyrazol-4-yl]-2-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]acetamide

HRID 1009741
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HRID 1009741 반응식
C(N(C(C)C)CC)(C)C.[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[N:18]=[CH:17][CH:16]=[C:15]2[O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]([OH:34])=O)=[CH:27][CH:26]=1.[NH2:35][C:36]1[CH:37]=[N:38][N:39]([CH2:41][CH2:42][O:43][CH3:44])[CH:40]=1>CN(C=O)C>[CH3:44][O:43][CH2:42][CH2:41][N:39]1[CH:40]=[C:36]([NH:35][C:32](=[O:34])[CH2:31][C:28]2[CH:29]=[CH:30][C:25]([O:24][C:15]3[C:14]4[C:19](=[CH:20][C:21]([O:22][CH3:23])=[C:12]([O:11][CH3:10])[CH:13]=4)[N:18]=[CH:17][CH:16]=3)=[CH:26][CH:27]=2)[CH:37]=[N:38]1
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 422818851-(2-methoxyethyl)-1H-pyrazol-4-amineHCID 596475402-(4-(6,7-Dimethoxyquinolin-4-yloxy)phenyl)acetic acid

생성물 1

HCID 67304719N-[1-(2-methoxyethyl)pyrazol-4-yl]-2-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]acetamide수율 38.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

실험 절차

Diisopropylethylamine (0.124 ml) and 2-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate(V) (0.247 g) were added in turn to a stirred mixture of 2-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]acetic acid (0.2 g), 4-amino-1-(2-methoxyethyl)pyrazole (0.092 g) and DMF (3 ml) and the resultant mixture was stirred at ambient temperature for 18 hours. The resultant mixture was evaporated and the residue was purified by column cliromatography on silica using a solvent gradient from 100:0 to 24:1 mixtures of methylene chloride and a 3.5M methanolic ammonia solution as eluent. There was thus obtained the title compound as a solid (0.106 g); 1H NMR: (DMSOd6) 3.21 (s, 3H), 3.62 (s, 2H), 3.63 (t, 2H), 3.92 (s, 3H), 3.94 (s, 3H), 4.12 (t, 2H), 6.47 (d, 1H), 7.22 (d, 2H), 7.4 (s, 1H), 7.44 (s, 1H), 7.45 (d, 2H), 7.49 (s, 1H), 7.89 (s, 1H), 8.47 (d, 1H), 10.2 (s, 1H); Mass Spectrum: M+H+ 463.

후처리

  1. customThe resultant mixture was evaporated
  2. customthe residue was purified by column cliromatography on silica using a solvent gradient from 100:0 to 24:1 mixtures of methylene chloride

출처 및 근거

ORD 기록
ord-024cd5c93b064d97a0cc8634866a39b3
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07973164B2

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