Azanium;hydrate → HCID 66620926, compound

HRID 415230Notes

Reaction equation

HRID 415230 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([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:2]=1.O.[NH4+:21]>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([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:2]=1

Participants

3

Reactant 2

HCID 22024077Azanium;hydrateHCID 66621160HCID 66621160, compound

Product 1

HCID 66620926HCID 66620926, compound

Procedure

Methyl 2-(pyridin-3-yl)benzo[d]oxazole-7-carboxylate (135 mg, 0.53 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-3-yl)benzo[d]oxazole-7-carboxamide a solid (39 mg, yield 31%). 1H-NMR (400 MHz, DMSO-d6) δ 7.50-7.54 (t, J=8 Hz, 1H), 7.65-7.69 (q, 1H), 7.65-7.69 (q, 1H), 7.85-7.87 (d, J=8 Hz, 1H), 7.91-7.93 (d, J=8 Hz, 2H), 7.99-8.01 (d, J=8 Hz, 1H), 8.64-8.66 (d, J=8 Hz, 1H), 8.81-8.82 (d, J=4 Hz, 1H), 9.46-9.47 (s, J=4 Hz, 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-51e6ac9978a24f8d92a579d8aa08ba5d
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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