HCID 67263771, compound → HCID 67263538, compound

HRID 1687942Notes

Reaction equation

HRID 1687942 reaction equation
C(OC([N:11]1[CH2:17][C:16]2[CH:18]=[C:19]([O:25][CH3:26])[C:20]([N+:22]([O-])=O)=[CH:21][C:15]=2[NH:14][C:13](=[O:27])[CH2:12]1)=O)C1C=CC=CC=1>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:22][C:20]1[C:19]([O:25][CH3:26])=[CH:18][C:16]2[CH2:17][NH:11][CH2:12][C:13](=[O:27])[NH:14][C:15]=2[CH:21]=1

Participants

5

Reactant 1

HCID 67263771HCID 67263771, compound

Product 1

HCID 67263538HCID 67263538, compoundYield 58.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-methoxy-8-nitro-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid benzyl ester (380 mg, 1.0 mmol) in ethyl acetate (50 mL) and ethanol (50 mL) was treated with 10% Pd on carbon (50 mg) and placed on a Paar shaker under an atmosphere of hydrogen gas (50 psi). After 18 hours LCMS indicated completion of reaction. The mixture was filtered and concentrated to give 8-amino-7-methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (122 mg, 53%) as a tan solid, used without further purification; 1H NMR (400 MHz, DMSO-d6) δ 9.42 (s, 1H), 6.64 (s, 1H), 6.33 (s, 1H), 4.72 (s, 2H), 3.72 (s, 3H), 3.67 (s, 2H), 3.19 (s, 2H); MS (m/e) 208 (M+1); mp 196° C. (dec.).

Workup

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

Sources & evidence

ORD record
ord-0a329698a2d842ab95d396dd80b2cd80
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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