HCID 131728508, compound → 2-Amino-4-chloro-6-methyl-10-oxo-10,11-dihydro-5-oxa-10lambda*4*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

HRID 1172541Notes

Reaction equation

HRID 1172541 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:25])[C:8]2[O:14][C:13]3[C:15]([Cl:22])=[CH:16][C:17]([N+:19]([O-])=O)=[CH:18][C:12]=3[CH2:11][S:10](=[O:23])[C:9]=2[CH:24]=1)=[O:4]>CN(C=O)C.[Ni]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:25])[C:8]2[O:14][C:13]3[C:15]([Cl:22])=[CH:16][C:17]([NH2:19])=[CH:18][C:12]=3[CH2:11][S:10](=[O:23])[C:9]=2[CH:24]=1)=[O:4]

Participants

4

Reactant 1

HCID 131728508HCID 131728508, compound

Product 1

HCID 1317285072-Amino-4-chloro-6-methyl-10-oxo-10,11-dihydro-5-oxa-10lambda*4*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of Example 154c (0.59 g, 1.54 mmol) in DMF (60 ml) was subjected to hydrogenation using activated Raney-Ni (0.3 g) at 50 psi for 3 h. It was filtered through a bed of celite, concentrated and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound. Yield: 0.39 g, (71%); 1H NMR (DMSO-d6): δ 2.6 (s, 3H, CH3), 3.88 (s, 3H, CH3), 4.65 (q, 2H, CH2), 5.6 (s, 2H, NH2), 6.65 (s, 2H, Ar), 8.0 (s, 1H, Ar), 8.16 (s, 1H, Ar); MS: m/e EI+) 351 (M+).

Workup

  1. customfor 3 h
  2. filtrationIt was filtered through a bed of celite,
  3. concentrationconcentrated
  4. custompurified

Sources & evidence

ORD record
ord-e5bf9c55b3674cd5a2b619d7c45fbb95
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

Loading…