HCID 70651980, compound → HCID 67995179, compound

HRID 2361397Notes

Reaction equation

HRID 2361397 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)=[C:6]([CH3:40])[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]>[Pd].O1CCCC1.CO>[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][C:6]=2[CH3:40])[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 1

HCID 70651980HCID 70651980, compound

Product 1

HCID 67995179HCID 67995179, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl 3-(1-carbamoyl-7-(2-methoxyethoxy)-3-methyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate (0.4846 g, 0.900 mmol) and 10% palladium on carbon (0.192 g, 0.180 mmol) in tetrahydrofuran (Ratio: 1.000, Volume: 23.99 ml) and methanol (Ratio: 1.5, Volume: 36.0 ml) was hydrogenated. After 1.5 h, the reaction was flushed with nitrogen, filtered through a wad of CELITE®, and rinsed. The filtrate was concentrated in vacuo, dissolved in EtOAc (100 mL), dried over MgSO4, filtered and concentrated in vacuo to give 4-(3-amino-2-methylphenyl)-7-(2-methoxyethoxy)-3-methyl-9H-pyrido[3,4-b]indole-1-carboxamide (0.3800 g, 0.846 mmol, 94% yield) as a solid, LC/MS (M+H)=405.18.

Workup

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

Sources & evidence

ORD record
ord-8ee401ed636d4d628503ca8628121c2e
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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