Pyridine → HCID 66621039, compound

HRID 415183Notes

Reaction equation

HRID 415183 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([NH2:19])=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[C:26](Cl)(=[O:28])[CH3:27]>ClCCl>[C:26]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([NH2:19])=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)[CH:5]=[CH:6][CH:7]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 66621296HCID 66621296, compound

Product 1

HCID 66621039HCID 66621039, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-aminophenyl)benzo[d]oxazole-4-carboxamide (100 mg, 0.39 mmol) in dichloromethane (5 mL) was added pyridine (34 mg, 0.43 mmol), then acetyl chloride (32 mg, 0.41 mmol) was added at 0° C. stirred at room temperature for 4 hr. The solvent was evaporated under reduced pressure and re-crystallized in methanol to obtain a white solid of 2-(3-acetamidophenyl)benzo[d]oxazole-4-carboxamide (45 mg, yield 38%). 1H-NMR (400 MHz, DMSO-d6) δ 2.09 (s, 3H), 7.53-7.58 (m, 2H), 7.84-7.86 (d, J=8 Hz, 1H), 7.97-8.07 (m, 4H), 8.44 (s, 1H), 8.57 (s, 1H), 10.29 (s, 1H); LC-MS (ESI) m/z 296 [M+1]+.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customre-crystallized in methanol

Sources & evidence

ORD record
ord-c8852b7cc4c8447fad62df877388d05e
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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