Sodium hydride → HCID 178481802, compound

HRID 1507072Notes

Reaction equation

HRID 1507072 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.O.[NH2:28][C:29]1[NH:33][N:32]=[N:31][N:30]=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:28][C:29]2[NH:33][N:32]=[N:31][N:30]=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 178509300HCID 178509300, compound

Product 1

HCID 178481802HCID 178481802, compoundYield 20.3%

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 (61.0 mg, 0.146 mmol) and 5-amino-1H-tetrazole monohydrate (42.5 mg, 0.500 mmol) in DMA (4 mL) was added NaH (30 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 (12.5 mg, 20%). LCMS m/z (%)=423 (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-b28d825b488548148876c153e6434681
Source dataset
uspto-grants-2015_12
Patent number
US09221755B2

Reaction notes

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