7-Methoxy-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid benzyl ester → 7-Methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one

HRID 1041603Notes

Reaction equation

HRID 1041603 reaction equation
C(OC([N:11]1[CH2:17][C:16]2[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:15]=2[NH:14][C:13](=[O:24])[CH2:12]1)=O)C1C=CC=CC=1>C(OCC)(=O)C.C(O)C.[Pd]>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:15]2[NH:14][C:13](=[O:24])[CH2:12][NH:11][CH2:17][C:16]=2[CH:18]=1

Participants

5

Reactant 1

HCID 672637677-Methoxy-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid benzyl ester

Product 1

HCID 672641827-Methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-oneYield 98.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-methoxy-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid benzyl ester (1.26 g, 3.86 mmol) in ethyl acetate (25 mL) and ethanol (25 mL) was treated with 10% Pd—C (125 mg) and hydrogenated under 40 psi H2 on a Paar apparatus. After two hours LCMS indicated completion of the reaction. The mixture was filtered and concentrated to afford 7-methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (730 mg, 96%) as a white solid, used without further purification; NMR (400 MHz, DMSO-d6) δ 9.60 (s, 1H), 7.00 (d, J=8 Hz, 1H), 6.80 (d, J=8 Hz, 1H), 6.78 (s, 1H), 3.80 (s, 2H), 3.72 (s, 3H), 3.38 (s, 2H), 3.00 (br, 1H); MS (m/e) 193 (M+1); mp 148° C.

Workup

  1. customcompletion of the reaction
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1a431f75b98b4f25a2943402d55618f6
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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