Methanamine, N-methoxy-, hydrochloride (1:1) → N-methoxy-N-methyl-1-(trifluoromethyl)cyclopropane-1-carboxamide

HRID 2202671Notes

Reaction equation

HRID 2202671 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]1([C:6](O)=[O:7])[CH2:5][CH2:4]1.Cl.CN(C)CCCN=C=NCC.Cl.[CH3:24][NH:25][O:26][CH3:27].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:27][O:26][N:25]([CH3:24])[C:6]([C:3]1([C:2]([F:10])([F:9])[F:1])[CH2:5][CH2:4]1)=[O:7]

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27783061-(Trifluoromethyl)cyclopropane-1-carboxylic acid

Product 1

HCID 57785368N-methoxy-N-methyl-1-(trifluoromethyl)cyclopropane-1-carboxamideYield 85.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-(trifluoromethyl)cyclopropanecarboxylic acid (150 mg, 0.974 mmol), 1-hydroxybenzotrizole monohydrate (224 mg, 1.46 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (280 mg, 1.46 mmol) and N,O-dimethylhydroxylamine hydrochloride (142 mg, 1.46 mmol) in DMF (5 mL) was added DIPEA (0.50 mL, 2.92 mmol) and the mixture was stirred at room temperature for overnight. The reaction mixture was quenched with water (30 mL) and extracted with EtOAc. The collected organic layer was washed with water and brine, dried over MgSO4 and concentrated under reduced pressure to provide compound A103-1 (164 mg, 85%) as a pale yellow oil.

Workup

  1. customThe reaction mixture was quenched with water (30 mL)
  2. extractionextracted with EtOAc
  3. washThe collected organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-39939a5ec2874878bd72263ece712493
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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