Dimethylformamide → N-(3-methoxyphenyl)-2-[4-(6,7-dimethoxyquinazolin-4-yloxy)phenyl]acetamide

HRID 1690478Notes

Reaction equation

HRID 1690478 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][N: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.[CH3:35][O:36][C:37]1[CH:38]=[C:39]([CH:41]=[CH:42][CH:43]=1)[NH2:40].CN(C=O)C>O>[CH3:35][O:36][C:37]1[CH:38]=[C:39]([NH:40][C:32](=[O:34])[CH2:31][C:28]2[CH:27]=[CH:26][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][N:16]=3)=[CH:30][CH:29]=2)[CH:41]=[CH:42][CH:43]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 108243-MethoxyanilineHCID 81531DiisopropylethylamineHCID 669066322-[4-(6,7-Dimethoxyquinazolin-4-yloxy)phenyl]acetic acid

Product 1

HCID 57396557N-(3-methoxyphenyl)-2-[4-(6,7-dimethoxyquinazolin-4-yloxy)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diisopropylethylamine (0.073 ml) and 2-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate(V) (0.16 g) were added in turn to a stirred mixture of 2-[4-(6,7-dimethoxyquinazolin-4-yloxy)phenyl]acetic acid (0.12 g), 3-methoxyaniline (0.047 ml) and DMF (3 ml) and the resultant mixture was stirred at ambient temperature for 2 hours. Water was added and the precipitate was recovered by filtration and purified by column chromatography on silica using a 19:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound as a solid (0.122 g); 1H NMR: (DMSOd6) 3.69 (s, 2H), 3.73 (s, 3H), 3.97 (s, 3H), 3.99 (s, 3H), 6.63 (m, 1H), 7.15 (d, 1H), 7.21 (m, 1H), 7.26 (d, 2H), 7.34 (m, 1H), 7.39 (s, 1H), 7.43 (d, 2H), 7.55 (s, 1H), 8.54 (s, 1H), 10.21 (s, 1H); Mass Spectrum: M+H+ 446.

Workup

  1. filtrationthe precipitate was recovered by filtration
  2. custompurified by column chromatography on silica using
  3. additiona 19:1 mixture of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-040b10dc05324b089912f3309a2a7ad2
Source dataset
uspto-grants-2012_04
Patent number
US08153643B2

Reaction notes

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