Azanium;hydrate → HCID 66621088, compound

HRID 415227Notes

Reaction equation

HRID 415227 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[O:8][C:9]3[C:15]([C:16]([O:18]C)=O)=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)=[CH:3][CH:2]=1.O.[NH4+:21]>>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[O:8][C:9]3[C:15]([C:16]([NH2:21])=[O:18])=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 22024077Azanium;hydrateHCID 66620804Methyl 2-(pyridin-4-yl)-1,3-benzoxazole-7-carboxylate

Product 1

HCID 66621088HCID 66621088, compoundYield 33%

Procedure

Methyl 2-(pyridin-4-yl)benzo[d]oxazole-7-carboxylate (130 mg, 0.51 mmol) in ammonium water (15 mL) was stirred at 25° C. overnight. The solvent was removed under reduced pressure. The crude product was purified by pre-HPLC to obtain 2-(pyridin-4-yl)benzo[d]oxazole-7-carboxamide as a solid (41 mg, yield 33%). 1H-NMR (400 MHz, DMSO-d6) δ 7.56-7.60 (t, J=8 Hz, 3H), 7.66-7.69 (q, 3H), 7.99-8.05 (q, 3H), 8.45 (s, 1H), 8.65-8.67 (d, J=8 Hz, 1H), 8.83-8.84 (d, J=4 Hz, 1H), 9.47 (s, 1H); LC-MS (ESI) m/z 240 [M+1]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe crude product was purified by pre-HPLC

Sources & evidence

ORD record
ord-8f9fae2a8dd2401e9f2f60620d327729
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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