1-[(2-Hydroxy-1,2-dimethylpropyl)amino]-7-(pyridin-3-ylethynyl)-5H-pyrido[4,3-b]indole-4-carboxamide → 1-[(2-Hydroxy-1,2-dimethylpropyl)amino]-7-(2-pyridin-3-ylethyl)-5H-pyrido[4,3-b]indole-4-carboxamide

HRID 1971006Notes

Reaction equation

HRID 1971006 reaction equation
[H][H].[OH:3][C:4]([CH3:33])([CH3:32])[CH:5]([NH:7][C:8]1[C:20]2[C:19]3[CH:18]=[CH:17][C:16]([C:21]#[C:22][C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)=[CH:15][C:14]=3[NH:13][C:12]=2[C:11]([C:29]([NH2:31])=[O:30])=[CH:10][N:9]=1)[CH3:6]>CCO.[Pd]>[OH:3][C:4]([CH3:32])([CH3:33])[CH:5]([NH:7][C:8]1[C:20]2[C:19]3[CH:18]=[CH:17][C:16]([CH2:21][CH2:22][C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)=[CH:15][C:14]=3[NH:13][C:12]=2[C:11]([C:29]([NH2:31])=[O:30])=[CH:10][N:9]=1)[CH3:6]

Participants

5

Reactant 2

HCID 595431631-[(2-Hydroxy-1,2-dimethylpropyl)amino]-7-(pyridin-3-ylethynyl)-5H-pyrido[4,3-b]indole-4-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 426360461-[(2-Hydroxy-1,2-dimethylpropyl)amino]-7-(2-pyridin-3-ylethyl)-5H-pyrido[4,3-b]indole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Hydrogen was bubbled through a solution of 1-[(2-hydroxy-1,2-dimethylpropyl)amino]-7-(pyridin-3-ylethynyl)-5H-pyrido[4,3-b]indole-4-carboxamide (10 mg, 0.024 mmol) and Pd/C (10%, 2.6 mg) in EtOH (1.3 mL). After complete conversion, the mixture was purged with nitrogen, filtered through a pad of Celite, and concentrate to afford the title compound. LRMS (APCI) calc'd for (C24H27N5O2) [M+H]+, 418.2. found 418.2.

Workup

  1. customAfter complete conversion, the mixture was purged with nitrogen
  2. filtrationfiltered through a pad of Celite
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-f261eab483834958bc6a3db1a4d739c9
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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