3,3,3-Trifluoropropanal → HCID 178434405, compound

HRID 2279130Notes

Reaction equation

HRID 2279130 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:29])[CH:5]=[CH:6][C:7]=1[C:8]1[N:13]=[C:12]2[NH:14][N:15]=[C:16]([CH3:17])[C:11]2=[C:10]([CH2:18][N:19]2[CH2:24][C:23]([CH3:26])([CH3:25])[NH:22][CH2:21][C:20]2([CH3:28])[CH3:27])[CH:9]=1.[F:30][C:31]([F:36])([F:35])[CH2:32][CH:33]=O.CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([OH:29])[CH:5]=[CH:6][C:7]=1[C:8]1[N:13]=[C:12]2[NH:14][N:15]=[C:16]([CH3:17])[C:11]2=[C:10]([CH2:18][N:19]2[CH2:24][C:23]([CH3:25])([CH3:26])[N:22]([CH2:33][CH2:32][C:31]([F:36])([F:35])[F:30])[CH2:21][C:20]2([CH3:28])[CH3:27])[CH:9]=1

Participants

7

Reactant 4

HCID 680283,3,3-TrifluoropropanalHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 178434404HCID 178434404, compound

Product 1

HCID 178434405HCID 178434405, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 300 mg of 3-fluoro-4-[3-methyl-4-(2,2,5,5-tetramethyl-piperazin-1-ylmethyl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-phenol, 387 mg 3,3,3-trifluoropropanal and 134 mg DIPEA in 6 ml dichloromethane and 6 ml THF was added 732 mg of sodium triacetoxyborohydride. The reaction was stirred at rt overnight. The solvents were removed in vacuo, and the residue was taken up in ethyl acetate and water. The pH was brought to neutral, 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. The residue was purified by HPLC and 214 mg (63%) of the title compound were obtained.

Workup

  1. customThe solvents were removed in vacuo
  2. customwere 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
  7. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-9663bda7466a4d58bb5048287d8aa04e
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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