Ammonium → HCID 44179987, compound

HRID 415313Notes

Reaction equation

[C:1]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([C:14]2[CH:15]=[C:16]([C:20]3[O:21][C:22]4[C:28]([C:29]([O:31]C)=O)=[CH:27][CH:26]=[CH:25][C:23]=4[N:24]=3)[CH:17]=[CH:18][CH:19]=2)=[O:13])[CH2:8][CH2:7]1)(=[O:5])[CH:2]([CH3:4])[CH3:3].[NH4+:33]>CO>[C:1]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([C:14]2[CH:15]=[C:16]([C:20]3[O:21][C:22]4[C:28]([C:29]([NH2:33])=[O:31])=[CH:27][CH:26]=[CH:25][C:23]=4[N:24]=3)[CH:17]=[CH:18][CH:19]=2)=[O:13])[CH2:8][CH2:7]1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 25 °C

Procedure

Methyl 2-(3-(4-isobutyrylpiperazine-1-carbonyl)phenyl)benzo[d]oxazole-7-carboxylate (150 mg, 0.34 mmol) was added to ammonium in methanol (10 mL) in a sealing tube and stirred at 25° C. for 3 days. The solvent was removed under reduced pressure. The crude product was purified by pre-HPLC to obtain 2-(3-(4-isobutyrylpiperazine-1-carbonyl)phenyl)benzo[d]oxazole-7-carboxamide as a white solid (20 mg, yield 14%). 1H-NMR (400 MHz, CD3OD) δ: 1.12-1.13 (d, J=6 Hz, 6H), 2.97 (brs, 1H), 3.55-3.85 (m, 8H), 7.50-7.54 (t, J=8.0 Hz, 1H), 7.71-7.75 (m, 2H), 7.91-7.95 (m, 2H), 8.41-8.45 (m, 2H); LC-MS (ESI) m/z: 421 (M+1)+.

Workup

customThe solvent was removed under reduced pressure
customThe crude product was purified by pre-HPLC

Sources & evidence

ORD record: ord-2a88ffeacbae45229c465c2ab1aeaa2c
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088760B2

Reaction notes

Loading…