HCID 67234282, compound → HCID 67234106, compound

HRID 2068559Notes

Reaction equation

HRID 2068559 reaction equation
C([O:8][C:9]1[CH:37]=[CH:36][C:12]([C:13]([NH:15][C:16]2([C:19](=[O:35])[NH:20][C@@H:21]3[CH2:27][CH2:26][C:25]4[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=4[N:23]4[CH:32]=[CH:33][N:34]=[C:22]34)[CH2:18][CH2:17]2)=[O:14])=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)C.[Pd]>[CH:32]1[N:23]2[C:24]3[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=3[CH2:26][CH2:27][C@@H:21]([NH:20][C:19]([C:16]3([NH:15][C:13](=[O:14])[C:12]4[CH:11]=[CH:10][C:9]([OH:8])=[CH:37][CH:36]=4)[CH2:17][CH2:18]3)=[O:35])[C:22]2=[N:34][CH:33]=1

Participants

4

Reactant 1

HCID 67234282HCID 67234282, compound

Product 1

HCID 67234106HCID 67234106, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Dissolve 4-benzyloxy-N-[1-[[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]carbamoyl]cyclopropyl]benzamide (145 mg, 294.37 μmoles) in ethanol (20 mL) and hydrogenate on a Parr shaker with 10% Pd/C (22.8 mg, 10.71 μmoles) for 18 hours (60 psi, ambient temperature). Filter off the catalyst and concentrate the filtrate under reduced pressure to give the title compound (107 mg, 90%) as a white solid: MS (m/z): 403 (M+1).

Workup

  1. filtrationFilter off the catalyst
  2. concentrationconcentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-d9301e8cdd3d4147b2ed6d27c964c4a4
Source dataset
uspto-grants-2012_10
Patent number
US08299061B2

Reaction notes

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