Methanol → n-[(2-Chloro-4-fluorophenyl)methyl]-1-cyclopropyl-5-oxoprolinamide

HRID 554099Notes

Reaction equation

HRID 554099 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N+:10]#[C-:11].[CH2:12]([CH:17]=O)[CH2:13][C:14](O)=[O:15].[CH:19]1([NH2:22])[CH2:21][CH2:20]1.C[OH:24]>>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][NH:10][C:11](=[O:24])[C@@H:17]1[CH2:12][CH2:13][C:14](=[O:15])[N:22]1[CH:19]1[CH2:21][CH2:20]1

Participants

5

Reactant 4

HCID 887MethanolHCID 11124-Oxobutanoic acidHCID 69828CyclopropylamineHCID 55265420HCID 55265420, compound

Product 1

HCID 67461861n-[(2-Chloro-4-fluorophenyl)methyl]-1-cyclopropyl-5-oxoprolinamide

Conditions

Temperature
100 °C

Procedure

To a solution of [2-chloro-4-fluoro-phenyl]methyl isocyanide (0.068 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 a colourless gum which was triturated with diethyl ether to give N-[(2-chloro-4-fluorophenyl)methyl]-1-cyclopropyl-5-oxoprolinamide as a pale cream solid (0.058 g). LC/MS [M+H]+=310, retention time=2.16 minutes.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified
  3. customto give a colourless gum which
  4. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-923525c43fe74607a548aa5c7651e57e
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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