HCID 49854431, compound → HCID 49836004, compound

HRID 1895545Notes

Reaction equation

HRID 1895545 reaction equation
[C:1]([C:4]1[C:12]2[N:11]=[C:10]([CH:13]3[CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:15][N:14]3C(OCC3C=CC=CC=3)=O)[NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[NH2:2]>CO.[Pd]>[CH2:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22][CH:13]([C:10]2[NH:9][C:8]3[CH:7]=[CH:6][CH:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:12]=3[N:11]=2)[NH:14]1

Participants

4

Reactant 1

HCID 49854431HCID 49854431, compound

Product 1

HCID 49836004HCID 49836004, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl 3-(4-carbamoyl-1H-benzo[d]imidazol-2-yl)-3,4-dihydroisoquinoline-2-(1H)-carboxylate (400 mg, 0.938 mmol) in methanol (20 ml) was added 10% Pd/C (40 mg) and the reaction mixture was degassed and stirred under H2 at 1 atmosphere pressure for 2 h at RT. The reaction mixture was filtered and the filtrate was concentrated and the crude was product further triturated with ether to afford 2-(1,2,3,4-tetrahydroisoquinolin-3-yl)-1H-benzo[d]imidazole-4-carboxamide. MS (ES+): m/z 293.1 [M+H]+

Workup

  1. customthe reaction mixture was degassed
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customfurther triturated with ether

Sources & evidence

ORD record
ord-24433fc570404661b42b431049361b32
Source dataset
uspto-grants-2013_08
Patent number
US08513433B2

Reaction notes

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