Ammonium Chloride → HCID 71258327, compound

HRID 1506138Notes

Reaction equation

HRID 1506138 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]([C:10]2[C:11]3[CH:18]=[CH:17][NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)=[O:9])[CH2:4][CH2:3]1.[F:19][C:20]([F:30])([F:29])[C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1.C(N(CC)C(C)C)(C)C.[Cl-].[NH4+]>C(#N)C.O>[N:13]1[C:12]2[NH:16][CH:17]=[CH:18][C:11]=2[C:10]([C:8]([CH:5]2[CH2:6][CH2:7][N:2]([CH2:25][C:24]3[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:29])[F:30])=[CH:28][CH:27]=3)[CH2:3][CH2:4]2)=[O:9])=[N:15][CH:14]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 86726614HCID 86726614, compound

Product 1

HCID 71258327HCID 71258327, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Piperidin-4-yl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)methanone hydrochloride (60.0 mg, 0.224 mmol) in acetonitrile (3 mL) was stirred with 4-(trifluoromethyl)benzyl bromide (70.0 mg, 0.292 mmol) and N,N-diisopropylethylamine (144 μL, 0.784 mmol) at 60° C. for 2 hours and allowed to cool to room temperature. After addition of water and saturated aqueous ammonium chloride, the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 (v/v)) to give the title compound as a pale yellow solid (65.0 mg, yield 75%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 (v/v))

Sources & evidence

ORD record
ord-24bda476fcbf44ee943bd4d84c1ee422
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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