Ammonia → 2-(4-(Pyridin-2-yl)phenyl)benzo[d]oxazole-7-carboxamide

HRID 415277Notes

Reaction equation

HRID 415277 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]3[C:21]([C:22](OC)=[O:23])=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:9][CH:8]=1.[NH3:26]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[CH:9][C:10]([C:13]2[O:14][C:15]3[C:21]([C:22]([NH2:26])=[O:23])=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66620654Methyl 2-(4-(pyridin-2-yl)phenyl)benzo[d]oxazole-7-carboxylate

Product 1

HCID 468302832-(4-(Pyridin-2-yl)phenyl)benzo[d]oxazole-7-carboxamideYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(4-(pyridin-2-yl)phenyl)benzo[d]oxazole-7-carboxylate (170 mg, 0.5 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. 110 mg of solid of 2-(4-(pyridin-2-yl)phenyl)benzo[d]oxazole-7-carboxamide was obtained. Yield: 69%. 1H-NMR (400 MHz, DMSO-d6) δ 7.43-7.45 (m, 1H), 7.50-7.53 (t, J=7.6 Hz, 1H), 7.83-7.85 (m, 1H), 7.89 (brs, 1H), 7.95-8.01 (m, 3H); 8.12-8.14 (d, J=8.0 Hz, 1H); 8.36-8.44 (q, 3H); 8.74-8.75 (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-06bc0edfd2474daaad9fe5ae4636c2db
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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