HCID 59787411, compound → HCID 72562237, compound

HRID 1965982Notes

Reaction equation

HRID 1965982 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][CH2:22][CH2:23][NH:24][C:25]([CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:26].[H][H]>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][CH2:22][CH2:23][NH:24][C:25]([CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31]1)=[O:26]

Participants

5

Reactant 2

HCID 59787411HCID 59787411, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 72562237HCID 72562237, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 7-chloro-6-[5-(cyclopentanecarbonyl-amino)-pent-1-ynyl]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (726 mg) in EtOAc (20 mL). Add 10% Pd/C (Degussa type, 100 mg) and then stir the mixture under 15 psi of hydrogen for 10 min. As reaction is not completed, add extra catalyst (147 mg) and stir under 15 psi of hydrogen for an extra 15 min. Filter the reaction mixture through a short pad of Celite® and concentrate in vacuo to obtain the desired intermediate that was used in the next step without further purification. MS (ES+) m/z=457.2 (M+H)+.

Workup

  1. customAs reaction
  2. filtrationFilter the reaction mixture through a short pad of Celite®
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-8097fe46ca1c4743b67bc3aabb130884
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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