Azanium;hydrate → HCID 66621077, compound

HRID 415219Notes

Reaction equation

[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([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:8]=[CH:9][CH:10]=1)[CH3:3].O.[NH4+:25]>C(O)C>[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([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:8]=[CH:9][CH:10]=1)[CH3:3]

Participants

Conditions

Temperature: 30 °C

Procedure

Methyl 2-(3-((dimethylamino)methyl)phenyl)benzo[d]oxazole-7-carboxylate (66 mg, 0.18 mmol) and ammonium water (50.4 mg, 1.44 mmol) were added to ethanol (30 mL) and the mixture was stirred at 30° C. for 1 hr. The resulting mixture was evaporated under reduced pressure and purified with Pre-HPLC to obtain 2-(3-((dimethylamino)methyl)phenyl)benzo[d]oxazole-7-carboxamide (12 mg, yield 22%). 1H-NMR (400 MHz, DMSO-d6) δ 2.88 (s, 5H), 4.36 (s, 2H), 7.02 (s, 1H), 7.37-7.41 (t, J=8 Hz, 1H), 7.54-7.61 (m, 2H), 7.84-7.86 (d, J=8 Hz, 1H), 7.97-7.99 (d, J=8 Hz, 1H), 8.28-8.29 (d, J=4 Hz, 1H), 8.50 (s, 1H); LC-MS (ESI) m/z 296 [M+1]+.

Workup

customThe resulting mixture was evaporated under reduced pressure
custompurified with Pre-HPLC

Sources & evidence

ORD record: ord-52a7354d75e64958a13a0690f29d9688
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088760B2

Reaction notes

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