Azanium;hydrate → 2-(4-((Dimethylamino)methyl)phenyl)benzo[d]oxazole-7-carboxamide

HRID 415210Notes

Reaction equation

HRID 415210 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[C:19]([C:20]([O:22]C)=O)=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:7][CH:6]=1)[CH3:3].O.[NH4+:25]>>[CH3:3][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[C:19]([C:20]([NH2:25])=[O:22])=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:7][CH:6]=1)[CH3:1]

Participants

3

Reactant 2

HCID 22024077Azanium;hydrateHCID 66620925Methyl 2-(4-((dimethylamino)methyl)phenyl)benzo[d]oxazole-7-carboxylate

Product 1

HCID 666214412-(4-((Dimethylamino)methyl)phenyl)benzo[d]oxazole-7-carboxamide

Procedure

Methyl 2-(4-((dimethylamino)methyl)phenyl)benzo[d]oxazole-7-carboxylate in ammonium water (10 mL) was stirred at 30° C. for 17 hr, then the solvents were evaporated and purified by pre-HPLC to obtain 2-(4-((dimethylamino)methyl)phenyl)benzo[d]oxazole-7-carboxamide as a white solid (10 mg). 1H-NMR (400 MHz, DMSO-d6) δ 2.18 (s, 6H), 3.5 (s, 2H), 7.47-7.49 (t, J=8 Hz, 1H), 7.54-7.56 (d, J=8.4 Hz, 2H), 7.79-7.81 (d, J=8 Hz, 1H), 7.86-7.90 (d, J=14.4 Hz, 2H), 7.94-7.96 (d, J=8 Hz, 1H), 8.24-8.26 (d, J=8 Hz, 2H); LC-MS (ESI) m/z 296 [M+1]+.

Workup

  1. customthe solvents were evaporated
  2. custompurified by pre-HPLC

Sources & evidence

ORD record
ord-098e7f8544554ba2bc426113e7d29bee
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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