Formic Acid → HCID 178501364, compound

HRID 642820Notes

Reaction equation

HRID 642820 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].[CH:41](O)=O>[Pd]>[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:21]=[C:22]([CH3:30])[C:23]4[NH:29][CH:41]=[N:26][C:24]=4[CH:25]=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

Participants

5

Reactant 3

HCID 284Formic AcidHCID 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 178501364HCID 178501364, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1.2 g (2.3 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 were dissolved in 50 mL formic acid and combined with 300 mg 10% Pd/C. The mixture was hydrogenated for 2 h in a Parr apparatus at 60° C. and 50 psi hydrogen pressure. Then the catalyst was filtered off, the filtrate was evaporated down i.vac. and the residue was purified by chromatography (Alox, gradient DCM/MeOH 40:1 to 30:1). Yield: 880 mg (76% of theory) ESI-MS: (M+H)+=506 Rf=0.40 (Polygram-Alox, DCM/MeOH 25:1)

Workup

  1. filtrationThen the catalyst was filtered off
  2. customthe filtrate was evaporated down i.vac
  3. customand the residue was purified by chromatography (Alox, gradient DCM/MeOH 40:1 to 30:1)

Sources & evidence

ORD record
ord-a4fe9bde18974729b825b4bece367375
Source dataset
uspto-grants-2010_04
Patent number
US07696195B2

Reaction notes

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