(R)-2-(4-amino-3-methyl-5-nitro-phenyl)-1-methoxycarbonyl-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate → (R)-2-(3,4-diamino-5-methyl-phenyl)-1-methoxycarbonyl-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

HRID 1864631Notes

Reaction equation

HRID 1864631 reaction equation
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@@H:18]([C:31]([O:33][CH3:34])=[O:32])[CH2:19][C:20]3[CH:25]=[C:24]([N+:26]([O-])=O)[C:23]([NH2:29])=[C:22]([CH3:30])[CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:35]=[CH:36][CH:37]=[CH:38][C:4]=2[NH:3]1.[H][H]>CO.[Pd]>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C@@H:18]([C:31]([O:33][CH3:34])=[O:32])[CH2:19][C:20]3[CH:21]=[C:22]([CH3:30])[C:23]([NH2:29])=[C:24]([NH2:26])[CH:25]=3)=[O:16])[CH2:13][CH2:14]2)[CH2:7][CH2:6][C:5]2[CH:35]=[CH:36][CH:37]=[CH:38][C:4]=2[NH:3]1

Participants

5

Reactant 2

HCID 68610153(R)-2-(4-amino-3-methyl-5-nitro-phenyl)-1-methoxycarbonyl-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 68676807(R)-2-(3,4-diamino-5-methyl-phenyl)-1-methoxycarbonyl-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 2.00 g (3.24 mmol) (R)-2-(4-amino-3-methyl-5-nitro-phenyl)-1-methoxycarbonyl-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate and 300 mg 10% Pd/C in 100 mL MeOH was hydrogenated for 3.5 h at 50° C. and 50 psi hydrogen pressure. The catalyst was filtered off, the filtrate was evaporated down i. vac. and the residue was purified by chromatography (silica gel, gradient DCM/MeOH 30:1 to DCM/MeOH 15:1).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated down i
  3. customand the residue was purified by chromatography (silica gel, gradient DCM/MeOH 30:1 to DCM/MeOH 15:1)

Sources & evidence

ORD record
ord-565da0d880c146559bda47df1d412e60
Source dataset
uspto-grants-2009_12
Patent number
US07625886B2

Reaction notes

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