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

HRID 2361296Notes

Reaction equation

HRID 2361296 reaction equation
[C:1]([C:4]1[C:9]2[NH:10][C:11]3[C:16]([C:8]=2[C:7]([C:23]2[C:24]([CH3:40])=[C:25]([NH:29]C(=O)OCC4C=CC=CC=4)[CH:26]=[CH:27][CH:28]=2)=[CH:6][N:5]=1)=[CH:15][CH:14]=[C:13]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[CH:12]=3)(=[O:3])[NH2:2]>C1COCC1.CO.[Pd]>[NH2:29][C:25]1[C:24]([CH3:40])=[C:23]([C:7]2[C:8]3[C:16]4[C:11](=[CH:12][C:13]([N:17]5[CH2:18][CH2:19][O:20][CH2:21][CH2:22]5)=[CH:14][CH:15]=4)[NH:10][C:9]=3[C:4]([C:1]([NH2:2])=[O:3])=[N:5][CH:6]=2)[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 1

HCID 67994345Benzyl 3-(1-carbamoyl-7-morpholino-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate

Product 1

HCID 679949134-(3-Amino-2-methylphenyl)-7-morpholino-9H-pyrido[3,4-b]indole-1-carboxamideYield 88.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl 3-(1-carbamoyl-7-morpholino-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate (0.2735 g, 0.511 mmol) and 10% Pd/C (0.109 g, 0.102 mmol) in THF (12.8 mL) and MeOH (19.2 mL) was hydrogenated. After 1.5 hr, the reaction was flushed with nitrogen and filtered through a wad of CELITE®. The filtrate was concentrated in vacuo, dissolved in CH2Cl2, dried over MgSO4, and concentrated in vacuo to give the desired product (0.196 g, 0.450 mmol, 88% yield) as a tan solid.

Workup

  1. customthe reaction was flushed with nitrogen
  2. filtrationfiltered through a wad of CELITE®
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutiondissolved in CH2Cl2
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c11551aa55d4cb089b08e0f09622122
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

Loading…