Acetic Acid → 1-[1-(4-Fluorophenyl)cyclobutyl]-7-{2-[(propylsulfonyl)amino]ethoxy}-3,4-dihydroisoquinoline-2(1H)-carboximidamide acetate

HRID 242074Notes

Reaction equation

HRID 242074 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[CH:20]=4)[CH2:15][CH2:14][N:13]3/[C:32](/[NH:44]C(=O)OCC3C=CC=CC=3)=[N:33]/C(=O)OCC3C=CC=CC=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:55]([OH:58])(=[O:57])[CH3:56].[H][H]>CO.[Pd]>[C:55]([OH:58])(=[O:57])[CH3:56].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[CH:20]=4)[CH2:15][CH2:14][N:13]3[C:32](=[NH:33])[NH2:44])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 88239773benzyl (NE)-N-[[1-[1-(4-fluorophenyl)cyclobutyl]-7-[2-(propylsulfonylamino)ethoxy]-3,4-dihydro-1H-isoquinolin-2-yl]-(phenylmethoxycarbonylamino)methylidene]carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 671890911-[1-(4-Fluorophenyl)cyclobutyl]-7-{2-[(propylsulfonyl)amino]ethoxy}-3,4-dihydroisoquinoline-2(1H)-carboximidamide acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dibenzyl [(E)-{1-[1-(4-fluorophenyl)cyclobutyl]-7-{2-[(propylsulfonyl)amino]ethoxy}-3,4-dihydroisoquinolin-2(1H)-yl}methylylidene]biscarbamate (95 mg, 0.126 mmol) was dissolved in methanol (8 mL) under an atmosphere of nitrogen. Acetic acid (0.4 mL) was added followed by 10% palladium on charcoal (40 mg, 0.038 mmol). The nitrogen was replaced by one atmosphere of hydrogen and the reaction mixture was stirred at room temperature for 3 h. The catalyst was removed by filtration and the solution of the product was concentrated in vacuo. The product was dissolved in ethanol (0.5 mL) and water (15 mL) and was lyophilized. Yield: 61 mg (0.125 mmol, 99%).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe solution of the product was concentrated in vacuo
  3. dissolutionThe product was dissolved in ethanol (0.5 mL)

Sources & evidence

ORD record
ord-c3c1a2e9ce3348a09ae768b87234a28e
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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