Ammonia → HCID 46847386, compound

HRID 415282Notes

Reaction equation

HRID 415282 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:14][C:15]4[C:21]([C:22](OC)=[O:23])=[CH:20][CH:19]=[CH:18][C:16]=4[N:17]=3)=[CH:9][CH:8]=2)[CH:2]=1.[NH3:26]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[O:14][C:15]4[C:21]([C:22]([NH2:26])=[O:23])=[CH:20][CH:19]=[CH:18][C:16]=4[N:17]=3)=[CH:11][CH:12]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66621211HCID 66621211, compound

Product 1

HCID 46847386HCID 46847386, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(4-(pyridin-3-yl)phenyl)benzo[d]oxazole-7-carboxylate (150 mg, 0.45 mmol) was added to ammonia in methanol (30 mL) and the mixture was stirred at room temperature for 3 days. Then the solid was filtered, washed with methanol, dried in vacuum. 120 mg of 2-(4-(pyridin-3-yl)phenyl)benzo[d]oxazole-7-carboxamide was obtained. Yield: 84%. 1H-NMR (400 MHz, DMSO-d6) δ 7.52-7.58 (m, 2H), 7.83-8.05 (m, 6H), 8.21-8.23 (m, 1H), 8.42-8.44 (d, J=8 Hz, 2H), 8.64-8.66 (m, 1H); 9.03-9.04 (m, 1H); LC-MS (ESI) m/z: 316 (M+1)+.

Workup

  1. filtrationThen the solid was filtered
  2. washwashed with methanol
  3. customdried in vacuum

Sources & evidence

ORD record
ord-75bf399abfc74cf58225ed402de74f17
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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