Azane;hydrate → HCID 66620997, compound

HRID 415241Notes

Reaction equation

HRID 415241 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:14](=[C:16]([C:20]([O:22]C)=O)[CH:17]=[CH:18][CH:19]=3)[N:15]=2)=[CH:7][CH:6]=1)[CH3:3].O.[NH3:25]>>[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[C:14](=[C:16]([C:20]([NH2:25])=[O:22])[CH:17]=[CH:18][CH:19]=3)[N:15]=2)=[CH:7][CH:6]=1)[CH3:3]

Participants

3

Reactant 2

HCID 12896473Azane;hydrateHCID 66621037HCID 66621037, compound

Product 1

HCID 66620997HCID 66620997, compoundYield 41.7%

Conditions

Temperature
30 °C

Procedure

Methyl 2-(4-((dimethylamino)methyl)phenyl)benzo[d]oxazole-4-carboxylate (40 mg, 0.13 mmol) and ammonia water (17.2 mg, 0.52 mmol) were added and the mixture was stirred at 30° C. for 1 h. The resulting mixture was evaporated under reduced pressure and purified by pre-HPLC. 2-(4-((dimethylamino)methyl)phenyl)benzo[d]oxazole-4-carboxamide (16 mg) was obtained, yield 41%. LC-MS (ESI) m/z: 296 (M+1)+. 1H-NMR (400 MHz, DMSO-d6): δ 2.94 (s, 6H), 4.46 (s, 2H), 7.57-7.58 (m, 1H), 7.75-7.77 (m, 2H), 7.93 (brs, 1H), 8.09 (brs, 1H), 8.43-8.44 (m, 2H).

Workup

  1. customThe resulting mixture was evaporated under reduced pressure
  2. custompurified by pre-HPLC

Sources & evidence

ORD record
ord-f8c0226185954a41b53265ad0aa70fce
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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