HCID 67265195, compound → HCID 67264274, compound

HRID 1687947Notes

Reaction equation

HRID 1687947 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]([CH2:5][N:6]1[C:12]2[CH:13]=[C:14]([N+:19]([O-])=O)[C:15]([O:17][CH3:18])=[CH:16][C:11]=2[CH2:10][N:9]([CH2:22][C:23]([N:25]([CH3:27])[CH3:26])=[O:24])[CH2:8][C:7]1=[O:28])=[O:4]>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:19][C:14]1[C:15]([O:17][CH3:18])=[CH:16][C:11]2[CH2:10][N:9]([CH2:22][C:23]([N:25]([CH3:27])[CH3:26])=[O:24])[CH2:8][C:7](=[O:28])[N:6]([CH2:5][C:3](=[O:4])[N:2]([CH3:1])[CH3:29])[C:12]=2[CH:13]=1

Participants

5

Reactant 1

HCID 67265195HCID 67265195, compound

Product 1

HCID 67264274HCID 67264274, compoundYield 100.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(1-dimethylcarbamoylmethyl-7-methoxy-8-nitro-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-N,N-dimethyl-acetamide (150 mg, 0.37 mmol) in ethyl acetate (25 mL) and ethanol (25 mL) was treated with 10% Pd—C and hydrogenated on a Paar apparatus under 40 psi H2. After 14 hours the mixture was filtered and concentrated to give 2-(8-amino-1-dimethylcarbamoylmethyl-7-methoxy-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-N,N-dimethyl-acetamide (140 mg, 99%) as a pale yellow solid, used without further purification; MS (m/e) 378 (M+1).

Workup

  1. filtrationAfter 14 hours the mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-2c33427a64d54ca3ac6e6f991e6c63c2
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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