Hydrochloric Acid → HCID 86588610, compound

HRID 2416739Notes

Reaction equation

HRID 2416739 reaction equation
[O:1]=[C:2]1[C@H:8]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:7][C:6]2[CH:14]=[CH:15][C:16]([O:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]3[N:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[CH:17][C:5]=2[CH2:4][N:3]1[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=1.Cl.[H][H]>[Pd].C(O)(=O)C>[O:1]=[C:2]1[C@H:8]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:7][C:6]2[CH:14]=[CH:15][C:16]([O:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]3[NH:28][CH2:27][CH2:26][CH2:25][N:24]=3)=[CH:17][C:5]=2[CH2:4][N:3]1[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 86588609HCID 86588609, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86588610HCID 86588610, compoundYield 118.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A Parr hydrogenation apparatus was charged with methyl (S)-3-oxo-8-[3-(pyrimidin-2-ylamino)-1-propyloxy]-2-[4-(trifluoromethyl)benzyl]-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (42 mg, 0.08 mmol), glacial acetic acid (2 mL), concentrated HCl (0.2 mL), and 10% Pd/C (10 mg). The mixture was shaken under hydrogen (40 psi) for 5 h, then the hydrogen was vented and the catalyst was removed by filtration through celite®. Evaporation of the solvents gave the crude title compound (52 mg) as a dark residue. This was used without further purification. MS (ES) m/e 547.2 (M+H)+.

Workup

  1. customthe catalyst was removed by filtration through celite®
  2. customEvaporation of the solvents

Sources & evidence

ORD record
ord-9f233c6428b0499f9b3c689abe5fbb58
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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