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

HRID 1009741
Notes
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Reaction equation

HRID 1009741 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-024cd5c93b064d97a0cc8634866a39b3
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07973164B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes