Potassium Hydroxide → HCID 86712746, compound

HRID 1779120Notes

Reaction equation

HRID 1779120 reaction equation
C([O-])(=O)C.[NH4+].[C:6]([C:9]1[N:14]=[CH:13][C:12]([NH:15][C:16]2[N:21]=[C:20]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH2:30][C:31]([NH2:33])=[O:32])[C:19]([C:34]([F:37])([F:36])[F:35])=[CH:18][N:17]=2)=[CH:11][CH:10]=1)(=O)[CH3:7].C([BH3-])#[N:39].[Na+].[OH-].[K+]>CO.C1COCC1>[NH2:39][CH:6]([C:9]1[N:14]=[CH:13][C:12]([NH:15][C:16]2[N:21]=[C:20]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH2:30][C:31]([NH2:33])=[O:32])[C:19]([C:34]([F:37])([F:35])[F:36])=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[CH3:7]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride2×HCID 86712744HCID 86712744, compound

Product 1

HCID 86712746HCID 86712746, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ammonium acetate (0.250 g, 3.23 mmol) was added to a solution of 2-(2-(2-(2-((6-acetylpyridin-3-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetamide (A143) (0.072 g, 0.162 mmol) in MeOH (4 mL) and THF (2 mL) and the mixture was stirred for 20 minutes under a nitrogen atmosphere. Sodium cyanoborohydride (7 mg, 0.1 mmol) was added and the mixture was stirred for 5 hours. Additional sodium cyanoborohydride (7 mg, 0.1 mmol) was added and the mixture was stirred for a total of 22 hours at 35° C. The aqueous phase was basified with solid potassium hydroxide (pH 10) and extracted with EtOAc (3×30 mL). The combined organic phases were washed with brine, dried (Na2SO4), and adsorbed on to silica. The product was purified by silica column chromatography (CombiFlash Rf, 12 g SiO2 Cartridge, 0-20% MeOH in DCM) to give the title compound (40) as a white solid (0.042 g, 58%). LCMS-B: 4.30 min; m/z 445 [M+H]+.

Workup

  1. stirringthe mixture was stirred for 5 hours
  2. stirringthe mixture was stirred for a total of 22 hours at 35° C
  3. extractionextracted with EtOAc (3×30 mL)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customThe product was purified by silica column chromatography (CombiFlash Rf, 12 g SiO2 Cartridge, 0-20% MeOH in DCM)

Sources & evidence

ORD record
ord-ee18a553f58042689d770f15b53f2d9c
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

Loading…