Ammonia → 2-(3-(Pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide

HRID 415304Notes

Reaction equation

HRID 415304 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([C:13]3[O:14][C:15]4[C:21]([C:22]([O:24]C)=O)=[CH:20][CH:19]=[CH:18][C:16]=4[N:17]=3)[CH:10]=[CH:11][CH:12]=2)=[CH:3][CH:2]=1.[NH3:26]>CO>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[CH:8]=[C:9]([C:13]3[O:14][C:15]4[C:21]([C:22]([NH2:26])=[O:24])=[CH:20][CH:19]=[CH:18][C:16]=4[N:17]=3)[CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66621012Methyl 2-(3-(pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxylate

Product 1

HCID 666209992-(3-(Pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxamideYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(3-(pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxylate (130 mg, 0.24 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 2-(3-(pyridin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide was obtained, yield: 88%. 1HNMR (400 MHz, DMSO-d6): δ7.52-7.54 (t, J=6.0 Hz, 1H), 7.56-7.59 (m, 1H), 7.77-7.80 (t, J=6.0 Hz, 1H), 7.86-7.88 (dd, J=6.4 Hz, 0.8 Hz, 1H), 7.92 (brs, 1H), 7.98 (brs, 1H), 8.00-8.03 (m, 2H), 8.22-8.24 (m, 1H), 8.36-8.38 (d, J=6.4 Hz, 1H), 8.61 (s, 1H), 8.65-8.67 (m, 1H), 9.03-9.04 (d, J=1.6 Hz, 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-c0839372032e4e9bb5a3b11b26447111
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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