Hydrochloric Acid → N-[(S)-5-(2-Hydroxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-2-methyl-N'-(2,2,3,3,3-pentafluoro-propyl)-malonamide

HRID 30997Notes

Reaction equation

HRID 30997 reaction equation
C([O:8][CH2:9][CH2:10][N:11]1[C:17](=[O:18])[C@@H:16]([NH:19][C:20](=[O:34])[CH:21]([CH3:33])[C:22]([NH:24][CH2:25][C:26]([F:32])([F:31])[C:27]([F:30])([F:29])[F:28])=[O:23])[C:15]2[CH:35]=[CH:36][CH:37]=[CH:38][C:14]=2[C:13]2[CH:39]=[CH:40][CH:41]=[CH:42][C:12]1=2)C1C=CC=CC=1.Cl>CO.[Pd]>[OH:8][CH2:9][CH2:10][N:11]1[C:17](=[O:18])[C@@H:16]([NH:19][C:20](=[O:34])[CH:21]([CH3:33])[C:22]([NH:24][CH2:25][C:26]([F:31])([F:32])[C:27]([F:29])([F:30])[F:28])=[O:23])[C:15]2[CH:35]=[CH:36][CH:37]=[CH:38][C:14]=2[C:13]2[CH:39]=[CH:40][CH:41]=[CH:42][C:12]1=2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58972538HCID 58972538, compound

Product 1

HCID 16742059N-[(S)-5-(2-Hydroxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-2-methyl-N'-(2,2,3,3,3-pentafluoro-propyl)-malonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N—[(S)-5-(2-Benzyloxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-2-methyl-N′-(2,2,3,3,3-pentafluoro-propyl)-malonamide (113 mg, 0.19 mmol) were dissolved in methanol (20 ml) and treated with 37% aqueous HCl (0.1 ml) and palladium on carbon (10%, 6 mg) and stirred for 2 days under an atmosphere of hydrogen. After filtration and evaporation of the solvent, the title compound was obtained as white solid (94%). MS: m/e=450(M+H+).

Workup

  1. filtrationAfter filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-4bd068d50b7b44519c2d0e295669bc6b
Source dataset
uspto-grants-2008_09
Patent number
US07425551B2

Reaction notes

Loading…