HCID 136359509, compound → 4-[3-(2-cyclohexyl-ethyl)-6-(4-hydroxy-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 82051Notes

Reaction equation

HRID 82051 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:17]3[C:31]([C:32]#[C:33][CH:34]4[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]4)=[N:30][N:29]([CH:40]4[CH2:45][CH2:44][CH2:43][CH2:42][O:41]4)[C:18]=3[N:19]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[CH:21]=2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]([C:16]2[C:17]3[C:31]([CH2:32][CH2:33][CH:34]4[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]4)=[N:30][N:29]([CH:40]4[CH2:45][CH2:44][CH2:43][CH2:42][O:41]4)[C:18]=3[N:19]=[C:20]([C:22]3[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=3)[CH:21]=2)=[O:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 136359509HCID 136359509, compound

Product 1

HCID 1363595084-[3-(2-cyclohexyl-ethyl)-6-(4-hydroxy-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-piperazine-1-carboxylic acid tert-butyl esterYield 95.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

To a solution of 4-[3-cyclohexylethynyl-6-(4-hydroxy-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester (0.34 g, 0.56 mmol) in methanol (15 ml) was added Pd/C (10%, 12 mg, 0.01 mmol). The reaction mixture was hydrogenated at 4 bar for 18 h, Pd/C (10%, 12 mg, 0.01 mmol) was added and hydrogenation pursued for an additional 8 hours. The reaction mixture was then filtered and concentrated under reduced pressure to yield the title compound (0.33 g, 95%) as a grey solid.

Workup

  1. waithydrogenation pursued for an additional 8 hours
  2. filtrationThe reaction mixture was then filtered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0f719562b684df5a38308d82960f514
Source dataset
uspto-grants-2014_09
Patent number
US08846712B2

Reaction notes

Loading…