Benzyl 3-(1-carbamoyl-6-morpholino-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate → 4-(3-Amino-2-methylphenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxamide

HRID 2361348Notes

Reaction equation

HRID 2361348 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][C:14]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[CH:13][CH:12]=3)(=[O:3])[NH2:2]>CO.C1COCC1.[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][CH:13]=[C:14]([N:17]5[CH2:18][CH2:19][O:20][CH2:21][CH2:22]5)[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 67994849Benzyl 3-(1-carbamoyl-6-morpholino-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate

Product 1

HCID 679946124-(3-Amino-2-methylphenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxamideYield 84.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl 3-(1-carbamoyl-6-morpholino-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate (0.125 g, 0.233 mmol) and 10% Pd/C (0.025 g, 0.023 mmol) in methanol (8.75 mL) and THF (2.92 mL) was stirred under a hydrogen balloon. After 1 hr, the reaction was flushed with nitrogen, filtered through a pad of CELITE®, rinsed with MeOH. The filtrate was concentrated in vacuo, dissolved in CH2Cl2 (100 mL), dried over MgSO4, and concentrated in vacuo to give the desired product (0.0786 g, 0.196 mmol, 84% yield) as a light tan solid.

Workup

  1. customthe reaction was flushed with nitrogen
  2. filtrationfiltered through a pad of CELITE®
  3. washrinsed with MeOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutiondissolved in CH2Cl2 (100 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eefaa0b7a75c43ec8bdfd419636387f0
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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