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

HRID 415205Notes

Reaction equation

[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[C:18]([C:19]([O:21]C)=O)=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1.O.[NH4+:24]>>[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[C:18]([C:19]([NH2:24])=[O:21])=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1

Participants

Reactant 2

HCID 22024077Azanium;hydrate

HCID 66621355Methyl 2-(4-((methylamino)methyl)phenyl)benzo[d]oxazole-7-carboxylate

Product 1

HCID 441810242-(4-((Methylamino)methyl)phenyl)benzo[d]oxazole-7-carboxamideYield 33%

Procedure

Methyl 2-(4-((methylamino)methyl)phenyl)benzo[d]oxazole-7-carboxylate (25 mg, 0.06 mmol) in ammonium water (2 mL) was stirred at 30° C. for 17 hr, then the solvents were evaporated and purified by pre-HPLC to obtain 2-(4-((methylamino)methyl)phenyl)benzo[d]oxazole-7-carboxamide as a white solid (25 mg, yield 33%). 1H-NMR (400 MHz, MeOH-d4) δ 2.07 (s, 1H), 2.30 (s, 3H), 3.78 (s, 2H), 7.45-7.49 (t, J=8 Hz, 1H), 7.57-7.59 (d, J=8 Hz, 2H), 7.79-7.81 (d, J=8 Hz, 1H), 7.86-7.95 (m, 3H), 8.24-8.26 (d, J=8 Hz, 2H); LC-MS (ESI) m/z 282 [M+1]+.

Workup

customthe solvents were evaporated
custompurified by pre-HPLC

Sources & evidence

ORD record: ord-29f030d64e1b43219238534b60d6e842
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088760B2

Reaction notes

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