Propionyl chloride → HCID 178460547, compound

HRID 386840Notes

Reaction equation

HRID 386840 reaction equation
[NH2:1][C:2]1[C:3]([C:7](=[N:17][OH:18])[NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([Cl:16])[CH:10]=2)=[N:4][O:5][N:6]=1.C(N(CC)C(C)C)(C)C.[C:28](Cl)(=[O:31])[CH2:29][CH3:30]>ClCCl>[NH2:1][C:2]1[C:3]([C:7](=[N:17][O:18][C:28](=[O:31])[CH2:29][CH3:30])[NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([Cl:16])[CH:10]=2)=[N:4][O:5][N:6]=1

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 178509312HCID 178509312, compound

Product 1

HCID 178460547HCID 178460547, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-amino-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide (0.1 g, 0.37 mmol) and N,N-diisopropylethylamine (0.16 mL, 0.92 mmol) in dichloromethane (4 mL) was treated with propanoyl chloride (38 μL, 0.44 mmol) and stirred for 1 h. The reaction mixture was concentrated and purified by preparative LCMS to give the desired product (57 mg, 47%). LCMS for C12H12ClFN5O3 (M+H)+: m/z=328.0.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-5a660dc959324ef09806af38c1eb9473
Source dataset
uspto-grants-2013_02
Patent number
US08372870B2

Reaction notes

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