Methanol → n-{[2-Chloro-3-(trifluoromethyl)phenyl]methyl}-1-cyclopropyl-5-oxoprolinamide

HRID 554096Notes

Reaction equation

HRID 554096 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][N+:13]#[C-:14].[CH2:15]([CH:20]=O)[CH2:16][C:17](O)=[O:18].[CH:22]1([NH2:25])[CH2:24][CH2:23]1.C[OH:27]>>[Cl:1][C:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][NH:13][C:14](=[O:27])[C@@H:20]1[CH2:15][CH2:16][C:17](=[O:18])[N:25]1[CH:22]1[CH2:24][CH2:23]1

Participants

5

Reactant 4

HCID 887MethanolHCID 11124-Oxobutanoic acidHCID 69828CyclopropylamineHCID 86617532[2-Chloro-3-(trifluoromethyl)phenyl]methyl isocyanide

Product 1

HCID 67458833n-{[2-Chloro-3-(trifluoromethyl)phenyl]methyl}-1-cyclopropyl-5-oxoprolinamide

Conditions

Temperature
100 °C

Procedure

To a solution of [2-chloro-3-(trifluoromethyl)phenyl]methyl isocyanide (0.088 g, 0.4 mmol) and succinic semialdehyde (15% in water, 0.26 ml, 0.4 mmol) in methanol (1.75 ml) was added cyclopropylamine (0.042 ml, 0.6 mmol). The mixture was heated to 100° C. for 30 minutes in a microwave reactor. The solvent was removed in vacuo and the residue was purified by mass-directed automated HPLC to give N-{[2-Chloro-3-(trifluoromethyl)phenyl]methyl}-1-cyclopropyl-5-oxoprolinamide (0.076 g) as a white solid. LC/MS [M+H]+=361/363, retention time=2.39 minutes.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified

Sources & evidence

ORD record
ord-e72dca0cbb154d2c813bcb2a1d5370a6
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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