N-[[1,6-Diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]-4-(5-hydroxypent-1-yn-1-yl)benzamide → N-[[1,6-Diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]-4-(5-hydroxypentyl)benzamide

HRID 385267Notes

Reaction equation

HRID 385267 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:35][CH3:36])=[C:10]([CH2:19][NH:20][C:21](=[O:34])[C:22]3[CH:27]=[CH:26][C:25]([C:28]#[C:29][CH2:30][CH2:31][CH2:32][OH:33])=[CH:24][CH:23]=3)[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]>C1COCC1.CO.[OH-].[OH-].[Pd+2]>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:35][CH3:36])=[C:10]([CH2:19][NH:20][C:21](=[O:34])[C:22]3[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33])=[CH:26][CH:27]=3)[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 58505289N-[[1,6-Diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]-4-(5-hydroxypent-1-yn-1-yl)benzamide

Product 1

HCID 58505267N-[[1,6-Diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]-4-(5-hydroxypentyl)benzamideYield 101.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Pd(OH)2 (200 mg) was added to a solution of Intermediate 32 (200 mg, 0.40 mmol) in THF/MeOH (5 mL each). The solution was treated with H2 at ambient pressure for 3 h. The reaction mixture was then filtered through a plug of celite. The plug was washed with MeOH (50 mL) and the solvent was concentrated in vacuo to afford the title compound as a pale yellow solid (200 mg). ES/MS calcd. for C28H40N5O3+ 494.3. found m/z=494.4 (M+H)+.

Workup

  1. additionThe solution was treated with H2 at ambient pressure for 3 h
  2. filtrationThe reaction mixture was then filtered through a plug of celite
  3. washThe plug was washed with MeOH (50 mL)
  4. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-7720c0d5ee174b8d9f23c74dff928c9c
Source dataset
uspto-grants-2013_02
Patent number
US08367829B2

Reaction notes

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