Ethanol → HCID 89544204, compound

HRID 2283426Notes

Reaction equation

HRID 2283426 reaction equation
[C:1]([C:9]1[C:10]([F:20])=[C:11]([C@H:16]([NH2:19])[CH2:17][CH3:18])[CH:12]=[CH:13][C:14]=1[Cl:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[C:24]([NH2:28])(=[O:27])[CH:25]=[CH2:26]>CO>[C:1]([C:9]1[C:10]([F:20])=[C:11]([C@H:16]([NH:19][CH2:26][CH2:25][C:24]([NH2:28])=[O:27])[CH2:17][CH3:18])[CH:12]=[CH:13][C:14]=1[Cl:15])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6579AcrylamideHCID 89544715HCID 89544715, compound

Product 1

HCID 89544204HCID 89544204, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To (1R)-1-(3-benzoyl-4-chloro-2-fluorophenyl)propan-1-amine (0.1 g, 0.34 mmol) in a microwave tube was added ethanol (0.4 ml) water (0.4 ml), acrylamide (0.025 g, 0.35 mmol) and MnCl2 (0.056 g, 0.28 mmol) heated 100° C., 200 W for a total of 1 hour. The reaction was diluted with MeOH and filtered and filtrate evaporated then purified by Prep HPLC to give 3-{[(1R)-1-(3-benzoyl-4-chloro-2-fluorophenyl)propyl]amino}-propanamide (0.047 g).

Workup

  1. customfor a total of 1 hour
  2. filtrationfiltered
  3. customfiltrate evaporated
  4. customthen purified by Prep HPLC

Sources & evidence

ORD record
ord-af8c5d1e4f414914a16374370e616fc2
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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