HCID 178423633, compound → HCID 69423825, compound

HRID 1375368Notes

Reaction equation

HRID 1375368 reaction equation
[CH3:1][C:2]1[C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][N:12]([C:13](=[O:44])[CH2:14][N:15]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[N:19]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:18](=[O:32])[C@H:17]([CH2:33][C:34]4[C:42]5[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=5)[NH:36][N:35]=4)[C:16]3=[O:43])[C:6]=2[CH:5]=[C:4]([CH3:45])[CH:3]=1>C(OCC)(=O)C.[Pd]>[CH3:1][C:2]1[C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][N:12]([C:13](=[O:44])[CH2:14][N:15]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[N:19]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:18](=[O:32])[C@H:17]([CH2:33][C:34]4[C:42]5[CH2:41][CH2:40][CH2:39][CH2:38][C:37]=5[NH:36][N:35]=4)[C:16]3=[O:43])[C:6]=2[CH:5]=[C:4]([CH3:45])[CH:3]=1

Participants

4

Reactant 1

HCID 178423633HCID 178423633, compound

Product 1

HCID 69423825HCID 69423825, compoundYield 13.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3R)-1-[2-(6,8-dimethyl-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)-2-oxoethyl]-3-(1H-indazol-3-ylmethyl)-5-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione (50 mg) in ethyl acetate (8 mL) was treated with 10% palladium on charcoal (300 mg). Placed under H2 environment (by balloon) and stirred at room temperature for 48 hours. Filtered through celite and concentrated to dryness. Chromatographed on silica gel (Hexane:Ethyl Acetate). Lyophilized the residue to yield the title compound as a white solid (6.6 mg)

Workup

  1. filtrationFiltered through celite and
  2. concentrationconcentrated to dryness
  3. customChromatographed on silica gel (Hexane:Ethyl Acetate)

Sources & evidence

ORD record
ord-6fdd154b74cd48f096e4135023c91864
Source dataset
uspto-grants-2007_01
Patent number
US07169773B2

Reaction notes

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