Hydrochloric Acid → HCID 86686778, compound

HRID 1403144Notes

Reaction equation

HRID 1403144 reaction equation
[F:1][CH:2]([F:38])[C:3]1[N:7]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([NH:20][CH:21]3[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]3)[N:9]=2)[C:6]2[CH:34]=[CH:35][CH:36]=[CH:37][C:5]=2[N:4]=1.CO.Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1>[F:38][CH:2]([F:1])[C:3]1[N:7]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([NH:20][CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[N:9]=2)[C:6]2[CH:34]=[CH:35][CH:36]=[CH:37][C:5]=2[N:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 86686779HCID 86686779, compound

Product 1

HCID 86686778HCID 86686778, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of tert-butyl 4-({4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-morpholin-4-ylpyrimidin-2-yl}amino)piperidine-1-carboxylate (63 mg) and methanol (1.3 mL) were added a 4 M solution of hydrogen chloride in 1,4-dioxane (0.15 mL), and the mixture was stirred at room temperature for 4 hours. The reaction mixture was neutralized by the addition of saturated aqueous sodium bicarbonate solution, and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by amino silica gel column chromatography (hexane:ethyl acetate=50:50) to obtain 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-morpholin-4-yl-N-piperidin-4-ylpyrimidin-2-amine (27 mg) as a pale yellow powder.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by amino silica gel column chromatography (hexane:ethyl acetate=50:50)

Sources & evidence

ORD record
ord-fda6325e5f124c17bfdf68625872058e
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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