Benzyl 3-(1-carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate → 4-(3-amino-2-methylphenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamide

HRID 2361276Notes

Reaction equation

HRID 2361276 reaction equation
[C:1]([C:4]1[C:9]2[NH:10][C:11]3[C:16]([C:8]=2[C:7]([C:22]2[C:23]([CH3:39])=[C:24]([NH:28]C(=O)OCC4C=CC=CC=4)[CH:25]=[CH:26][CH:27]=2)=[CH:6][N:5]=1)=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][O:20][CH3:21])[CH:12]=3)(=[O:3])[NH2:2]>O1CCCC1.CO.[Pd]>[NH2:28][C:24]1[C:23]([CH3:39])=[C:22]([C:7]2[C:8]3[C:16]4[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:14][CH:15]=4)[NH:10][C:9]=3[C:4]([C:1]([NH2:2])=[O:3])=[N:5][CH:6]=2)[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 1

HCID 67995010Benzyl 3-(1-carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate

Product 1

HCID 679945404-(3-amino-2-methylphenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamideYield 102.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of benzyl 3-(1-carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate (0.226 g, 0.431 mmol) and Pd/C (60 mg, 0.056 mmol) in tetrahydrofuran (12 mL) and methanol (18 mL) was stirred at room temperature under H2, provided with a H2 balloon, for 1.5 hr. The catalyst was removed by suction filtration, and the filtrate was concentrated under vacuum. The residue was dissolved in ethyl acetate (80 mL) and dried over anhydrous MgSO4. Removal of the solvent under vacuum provided the desired product (0.172 g, 0.441 mmol, 102% yield) as a beige solid.

Workup

  1. customprovided with a H2 balloon, for 1.5 hr
  2. customThe catalyst was removed by suction filtration
  3. concentrationthe filtrate was concentrated under vacuum
  4. dissolutionThe residue was dissolved in ethyl acetate (80 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. customRemoval of the solvent under vacuum

Sources & evidence

ORD record
ord-cbac79f07aa8467ebad9681241c98514
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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