Sodium hydride → HCID 178481801, compound

HRID 1507073Notes

Reaction equation

HRID 1507073 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[CH:7][C:6]=1[C:21]1[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=1.[NH2:27][C:28]1[N:32]=[CH:31][NH:30][N:29]=1.[H-].[Na+]>CC(N(C)C)=O>[F:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[C:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:27][C:28]2[N:32]=[CH:31][NH:30][N:29]=2)=[C:6]([C:21]2[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=2)[CH:7]=1)=[O:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 58964266HCID 58964266, compoundHCID 178418311HCID 178418311, compound

Product 1

HCID 178481801HCID 178481801, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-(4-(2-bromoethoxy)-3-(1-methyl-1H-pyrazol-5-yl)phenyl)-3-fluorobenzamide (62.3 mg, 0.149 mmol) and 3-amino-1H-1,2,4-triazole (38.8 mg, 0.461 mmol) in DMA (4 mL) was added NaH (58.8 mg, 60% dispersion in mineral oil) and the reaction was stirred for two hours. The resulting material was purified by HPLC. The product was dried under reduced pressure to afford the title compound as a white solid (30.2 mg, 48%). LCMS m/z (%)=422 (M+H, 100).

Workup

  1. customThe resulting material was purified by HPLC
  2. customThe product was dried under reduced pressure

Sources & evidence

ORD record
ord-9fe32ca4495a4b0487ff857e1374ab9b
Source dataset
uspto-grants-2015_12
Patent number
US09221755B2

Reaction notes

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