Ammonium → HCID 44181680, compound

HRID 415318Notes

Reaction equation

HRID 415318 reaction equation
[CH:1]1([C:4]([N:6]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:15]=[C:16]([C:20]4[O:21][C:22]5[C:28]([C:29]([O:31]C)=O)=[CH:27][CH:26]=[CH:25][C:23]=5[N:24]=4)[CH:17]=[CH:18][CH:19]=3)=[O:13])[CH2:8][CH2:7]2)=[O:5])[CH2:3][CH2:2]1.[NH4+:33]>CO>[CH:1]1([C:4]([N:6]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:15]=[C:16]([C:20]4[O:21][C:22]5[C:28]([C:29]([NH2:33])=[O:31])=[CH:27][CH:26]=[CH:25][C:23]=5[N:24]=4)[CH:17]=[CH:18][CH:19]=3)=[O:13])[CH2:8][CH2:7]2)=[O:5])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 223AmmoniumHCID 66621372HCID 66621372, compound

Product 1

HCID 44181680HCID 44181680, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Methyl 2-(3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)phenyl)benzo[d]oxazole-7-carboxylate (130 mg, 0.33 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-(cyclopropanecarbonyl)piperazine-1-carbonyl)phenyl)benzo[d]oxazole-7-carboxamide (30 mg, yield 22%). 1H-NMR (400 MHz, CD3OD) δ: 0.85-0.92 (m, 4H), 1.29 (m, 1H), 3.20-3.99 (m, 8H), 7.52-7.56 (t, J=8.0 Hz, 1H), 7.74-7.75 (m, 2H), 7.92-7.97 (m, 2H), 8.43-8.47 (m, 2H); LC-MS (ESI) m/z: 419 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-0586935728504534a0ae8c2c75a2e3e9
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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