Acetic Acid → HCID 90013829, compound

HRID 2279143Notes

Reaction equation

HRID 2279143 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]3[N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[N:18]=[C:19]([CH3:20])[C:14]3=[C:13]([CH2:27][N:28]3[CH2:33][C:32]([CH3:35])([CH3:34])[NH:31][CH2:30][C:29]3([CH3:37])[CH3:36])[CH:12]=2)=[CH:7][CH:6]=1.[F:38][C:39]([F:44])([F:43])[CH2:40][CH:41]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(OCC)(=O)C.O>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:16]=[C:15]3[N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[N:18]=[C:19]([CH3:20])[C:14]3=[C:13]([CH2:27][N:28]3[CH2:33][C:32]([CH3:35])([CH3:34])[N:31]([CH2:41][CH2:40][C:39]([F:44])([F:43])[F:38])[CH2:30][C:29]3([CH3:37])[CH3:36])[CH:12]=2)=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 680283,3,3-Trifluoropropanal3×HCID 5049666Sodium triacetoxyborohydride3×HCID 90013940HCID 90013940, compound

Product 1

HCID 90013829HCID 90013829, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 150 mg of 6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-4-(2,2,5,5-tetramethyl-piperazin-1-ylmethyl)-1H-pyrazolo[3,4-b]pyridine, 33 mg 3,3,3-trifluoropropanal and 5 mg of acetic acid in 2 ml dichloromethane was added 94 mg of sodium triacetoxyborohydride. After 1 h at rt 33 mg 3,3,3-trifluoropropanal and 94 mg of sodium triacetoxyborohydride were added and the reaction was stirred overnight. Then another 33 mg 3,3,3-trifluoropropanal and 94 mg of sodium triacetoxyborohydride were added and the reaction was stirred overnight. The reaction was diluted with ethyl acetate and water. The pH was adjusted to 8, and the phases were separated. The aqueous phase was extracted with ethyl acetate twice. The combined organic phases were dried over sodium sulphate, filtrated and concentrated in vacuo. 167 mg (94%) of the title compound were obtained.

Workup

  1. stirringthe reaction was stirred overnight
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with ethyl acetate twice
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9963c53d96d5438db467c45a588b991f
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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