Azanium;hydrate → HCID 66621392, compound

HRID 415221Notes

Reaction equation

HRID 415221 reaction equation
[N:1]1([CH2:6][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)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.[NH4+:27]>C(O)C>[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]([C:13]3[O:14][C:15]4[C:21]([C:22]([NH2:27])=[O:24])=[CH:20][CH:19]=[CH:18][C:16]=4[N:17]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 22024077Azanium;hydrateHCID 66621401Methyl 2-(3-(pyrrolidin-1-ylmethyl)phenyl)benzo[d]oxazole-7-carboxylate

Product 1

HCID 66621392HCID 66621392, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

Methyl 2-(3-(pyrrolidin-1-ylmethyl)phenyl)benzo[d]oxazole-7-carboxylate (56 mg, 0.18 mmol) and ammonium water (50.4 mg, 1.44 mmol) were added to ethanol (30 mL) and the mixture was stirred at 30° C. for 1 hr. The resulting mixture was evaporated under reduced pressure and purified with Pre-HPLC to obtain 2-(3-(pyrrolidin-1-ylmethyl)phenyl)benzo[d]oxazole-7-carboxamide (14 mg, yield 22%). 1H-NMR (400 MHz, DMSO-d6) δ 1.92 (s, 4H), 3.19 (s, 4H), 4.42 (s, 2H), 7.49 (s, 1H), 7.70-7.94 (m, 6H), 8.35-8.43 (d, J=32 Hz, 2H); LC-MS (ESI) m/z 322 [M+1]+.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure
  2. custompurified with Pre-HPLC

Sources & evidence

ORD record
ord-e4e884d966414b15875d86cf66f8dab0
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

Loading…