Azanium;hydrate → HCID 66620923, compound

HRID 415208Notes

Reaction equation

HRID 415208 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:20]([O:22]C)=O)[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([CH2:16][NH:17][CH3:18])=[CH:12][CH:11]=3)=[N:7][C:6]=2[CH:19]=1.O.[NH4+:25]>>[F:1][C:2]1[CH:3]=[C:4]([C:20]([NH2:25])=[O:22])[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([CH2:16][NH:17][CH3:18])=[CH:12][CH:11]=3)=[N:7][C:6]=2[CH:19]=1

Participants

3

Reactant 2

HCID 22024077Azanium;hydrateHCID 66621247HCID 66621247, compound

Product 1

HCID 66620923HCID 66620923, compoundYield 22%

Procedure

Methyl 5-fluoro-2-(4-((methylamino)methyl)phenyl)benzo[d]oxazole-7-carboxylate (25 mg, 0.06 mmol) in ammonium water (2 mL) was stirred at 30° C. for 17 hr and the solvents were evaporated; the residue was purified by pre-HPLC to obtain 5-fluoro-2-(4-((methylamino)methyl)phenyl)benzo[d]oxazole-7-carboxamide as a white solid (4 mg, yield 22%). 1H-NMR (400 MHz, MeOD-d4) δ 2.07 (s, 1H), 2.41 (s, 3H), 3.85 (s, 2H), 7.52-7.55 (m, 2H), 7.57-7.61 (m, 2H), 8.25-8.27 (d, J=7.6 Hz, 2H); LC-MS (ESI) m/z 300 [M+1]+.

Workup

  1. customthe solvents were evaporated
  2. customthe residue was purified by pre-HPLC

Sources & evidence

ORD record
ord-45eb794d3c024fec9e49a1aabb2ae3bc
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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