Morpholine → HCID 86686783, compound

HRID 1403148Notes

Reaction equation

HRID 1403148 reaction equation
[F:1][CH:2]([F:37])[C:3]1[N:7]([C:8]2[N:13]=[C:12](S(C)=O)[N:11]=[C:10]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21][CH2:20]3)[CH:9]=2)[C:6]2[CH:33]=[CH:34][CH:35]=[CH:36][C:5]=2[N:4]=1.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.CN(C)C(=O)C>O>[F:1][CH:2]([F:37])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)[N:11]=[C:10]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21][CH2:20]3)[CH:9]=2)[C:6]2[CH:33]=[CH:34][CH:35]=[CH:36][C:5]=2[N:4]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 31374DimethylacetamideHCID 86686784HCID 86686784, compound

Product 1

HCID 86686783HCID 86686783, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of tert-butyl 4-[({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(methylsulfinyl)pyrimidin-4-yl}oxy)methyl]piperidine-1-carbamate (240 mg), morpholine (0.3 mL), and N,N-dimethylacetamide (2 mL) was stirred at room temperature for 1 hour. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and then the residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30-50:50) to obtain tert-butyl 4-[({6-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-2-(morpholin-4-yl)pyrimidin-4-yl}oxy)methyl]piperidine-1-carbamate (246 mg) as a white powder.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30-50:50)

Sources & evidence

ORD record
ord-a4d2b297c14b4c288a522d025875667f
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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