HCID 90013834, compound → HCID 90013594, compound

HRID 2279157Notes

Reaction equation

HRID 2279157 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][O:29][CH3:30])=[CH:23][CH:22]=3)[N:18]=[C:17]3[N:31]([CH:35]4[CH2:40][CH2:39][CH2:38][CH2:37][O:36]4)[N:32]=[C:33]([CH3:34])[C:16]=23)[CH2:10][C@H:9]1[CH2:41][C:42]([F:45])([F:44])[F:43])C1C=CC=CC=1>ClCCl>[CH3:30][O:29][CH2:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([C:19]2[N:18]=[C:17]3[N:31]([CH:35]4[CH2:40][CH2:39][CH2:38][CH2:37][O:36]4)[N:32]=[C:33]([CH3:34])[C:16]3=[C:15]([CH2:14][N:11]3[CH2:12][CH2:13][NH:8][C@H:9]([CH2:41][C:42]([F:45])([F:44])[F:43])[CH2:10]3)[CH:20]=2)=[CH:22][CH:23]=1

Participants

3

Reactant 1

HCID 90013834HCID 90013834, compound

Product 1

HCID 90013594HCID 90013594, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

217 mg of 4-[(R)-4-Benzyl-3-(2,2,2-trifluoro-ethyl)-piperazin-1-ylmethyl]-6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine were dissolved in 2.5 ml dichloromethane and 2.5 ml methanol and purged with argon. 22 mg Palladium (10% on charcoal) were added and the mixture was hydrogenated at 5 bar and at r.t. for 1.5 h. The catalyst was filtered off using celite and the solvents were evaporated. 188 mg (100%) of the crude title compound were obtained, which were used in the next step without further purification.

Workup

  1. custom2.5 ml methanol and purged with argon
  2. addition22 mg Palladium (10% on charcoal) were added
  3. filtrationThe catalyst was filtered off
  4. customthe solvents were evaporated

Sources & evidence

ORD record
ord-6d79cb55454b4394862b0d246dac71a6
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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