Hydrochloric Acid → HCID 73056321, compound

HRID 1779115Notes

Reaction equation

HRID 1779115 reaction equation
C([O-])(=O)C.[NH4+].[C:6]([C:9]1[CH:10]=[C:11]([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]([Cl:34])=[CH:18][N:17]=2)[CH:12]=[CH:13][CH:14]=1)(=O)[CH3:7].C([BH3-])#[N:36].[Na+].Cl>CO.O>[NH2:36][CH:6]([C:9]1[CH:10]=[C:11]([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]([Cl:34])=[CH:18][N:17]=2)[CH:12]=[CH:13][CH:14]=1)[CH3:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride2×HCID 86712742HCID 86712742, compound

Product 1

HCID 73056321HCID 73056321, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ammonium acetate (0.339 g, 4.40 mmol) was added to a solution of 2-(2-(2-(2-((3-acetylphenyl)amino)-5-chloropyrimidin-4-yl)ethyl)phenyl)acetamide (A141) (0.120 g, 0.293 mmol) in MeOH (5 mL) and the mixture was stirred for 20 minutes under a nitrogen atmosphere. Sodium cyanoborohydride (0.013 g, 0.21 mmol) was added and the mixture was stirred for 6 hours. Additional sodium cyanoborohydride (0.013 g, 0.21 mmol) was added and the mixture was stirred for 16 hours at room temperature. The mixture was diluted with water (10 mL), acidified with 20% aqueous HCl (10 mL) and washed with Et2O (2×30 mL). The aqueous phase was basified with solid potassium hydroxide to pH 10 and extracted with DCM (3×30 mL). The combined organic phases were washed with water, brine, dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was adsorbed onto silica gel and purified by column chromatography (CombiFlash Rf, 12 g SiO2 Cartridge, 0-30% MeOH in DCM) to give the title compound (38) as a white foam (0.057 g, 47%). LCMS-B: rt 5.45 min; m/z 410 [M+H]+.

Workup

  1. stirringthe mixture was stirred for 6 hours
  2. stirringthe mixture was stirred for 16 hours at room temperature
  3. washwashed with Et2O (2×30 mL)
  4. extractionextracted with DCM (3×30 mL)
  5. washThe combined organic phases were washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. customthe solvent evaporated in vacuo
  8. custompurified by column chromatography (CombiFlash Rf, 12 g SiO2 Cartridge, 0-30% MeOH in DCM)

Sources & evidence

ORD record
ord-2ab785978fdb4aac8d754e1953dc3c13
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

Loading…