Azanium;hydrate → HCID 66620892, compound

HRID 415223Notes

Reaction equation

HRID 415223 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([C:14]3[O:15][C:16]4[C:22]([C:23]([O:25]C)=O)=[CH:21][CH:20]=[CH:19][C:17]=4[N:18]=3)[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.O.[NH4+:28]>C(O)C>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([C:14]3[O:15][C:16]4[C:22]([C:23]([NH2:28])=[O:25])=[CH:21][CH:20]=[CH:19][C:17]=4[N:18]=3)[CH:11]=[CH:12][CH:13]=2)[CH2:2][CH2:3][NH:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 22024077Azanium;hydrateHCID 66621178Methyl 2-(3-(piperazin-1-ylmethyl)phenyl)benzo[d]oxazole-7-carboxylate

Product 1

HCID 66620892HCID 66620892, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

Methyl 2-(3-(piperazin-1-ylmethyl)phenyl)benzo[d]oxazole-7-carboxylate (79 mg, 0.23 mmol) and ammonium water (64.4 mg, 1.84 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-(piperazin-1-ylmethyl)phenyl)benzo[d]oxazole-7-carboxamide (12 mg, yield 13%). 1H-NMR (400 MHz, DMSO-d6) δ 2.91 (s, 4H), 3.21 (s, 4H), 4.20 (s, 2H), 7.48-7.52 (t, J=8 Hz, 1H), 7.67 (s, 2H), 7.81-7.97 (m, 4H), 8.31 (s, 2H); LC-MS (ESI) m/z 337 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-c46d87d916094bf6a6df34d3623cca70
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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