Sodium hydride → HCID 178481801, compound

HRID 1425505Notes

Reaction equation

HRID 1425505 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-5ba2afc0c5054fd59772b097229a341f
Source dataset
uspto-grants-2015_01
Patent number
USRE045337E1

Reaction notes

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