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

HRID 1850854Notes

Reaction equation

HRID 1850854 reaction equation
C(OC(=O)[NH:10]/[C:11](/[N:23]1[CH2:32][CH2:31][C:30]2[C:25](=[CH:26][C:27]([O:33][CH2:34][CH2:35][NH:36][S:37]([CH2:40][CH2:41][CH3:42])(=[O:39])=[O:38])=[CH:28][CH:29]=2)[CH:24]1[C:43]1([C:47]2[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=2)[CH2:46][CH2:45][CH2:44]1)=[N:12]\C(=O)OCC1C=CC=CC=1)C1C=CC=CC=1.[C:55]([OH:58])(=[O:57])[CH3:56].[H][H]>CO.[Pd]>[C:55]([OH:58])(=[O:57])[CH3:56].[F:53][C:50]1[CH:51]=[CH:52][C:47]([C:43]2([CH:24]3[C:25]4[C:30](=[CH:29][CH:28]=[C:27]([O:33][CH2:34][CH2:35][NH:36][S:37]([CH2:40][CH2:41][CH3:42])(=[O:39])=[O:38])[CH:26]=4)[CH2:31][CH2:32][N:23]3[C:11](=[NH:10])[NH2:12])[CH2:46][CH2:45][CH2:44]2)=[CH:48][CH:49]=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-484449f314604a63a075da36eb668cd7
Source dataset
uspto-grants-2015_02
Patent number
US08957089B2

Reaction notes

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