HCID 86622785, compound → HCID 86622786, compound

HRID 1965986Notes

Reaction equation

HRID 1965986 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[C:19]#[C:20][CH2:21][NH:22][C:23]([CH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:24]>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:13])([F:14])[F:15])[CH2:9][CH2:10][C:4]=2[C:3]=1/[CH:19]=[CH:20]\[CH2:21][NH:22][C:23]([CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29]1)=[O:24]

Participants

4

Reactant 1

HCID 86622785HCID 86622785, compound

Product 1

HCID 86622786HCID 86622786, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 7-chloro-6-[3-(cyclopentanecarbonyl-amino)-prop-1-ynyl]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (170 mg, 0.4 mmol) in EtOAc (50 mL) and submit the mixture to hydrogenation over 10% Pd/C (85 mg) at 15 psi for 10 mins. Filter the mixture through Celite® and concentrate the filtrate to give 7-chloro-6-[(Z)-3-(cyclopentanecarbonyl-amino)-propenyl]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a pale yellow solid (170 mg).

Workup

  1. customfor 10 mins
  2. filtrationFilter the mixture through Celite®
  3. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-e06283a3c0354dbaad93dc69cae66817
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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