HCID 86689308, compound → HCID 56603229, compound

HRID 1852494Notes

Reaction equation

HRID 1852494 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([N:15]2[C:21](=[O:22])[CH2:20][C:19](=[O:23])[NH:18][C:17]3[C:24]4[CH2:25][CH2:26][CH2:27][CH2:28][C:29]=4[CH:30]=[CH:31][C:16]2=3)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>O1CCCC1.CO.[C].[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([N:15]2[C:21](=[O:22])[CH2:20][C:19](=[O:23])[NH:18][C:17]3[C:24]4[CH2:25][CH2:26][CH2:27][CH2:28][C:29]=4[CH:30]=[CH:31][C:16]2=3)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 1

HCID 86689308HCID 86689308, compound

Product 1

HCID 56603229HCID 56603229, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-(3-Benzyloxyphenyl)-8,9,10,11-tetrahydronaphtho[2,1-b][1,4]diazepine-2,4(3H,5H)-dione (58 mg, 0.14 mmol) was dissolved in tetrahydrofuran (3 mL)-methanol (3 mL). To the solution was added 10% palladium-carbon (6 mg). The mixture was stirred under hydrogen atmosphere at room temperature for 6 hours. Insoluble was removed by filtration. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=50/1) to give the titled compound as slightly yellow crystal (30 mg, yield 66%).

Workup

  1. customInsoluble was removed by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-3049bb5ffc7f4c74924299a56094799f
Source dataset
uspto-grants-2015_02
Patent number
US08962613B2

Reaction notes

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