Water → HCID 86692143, compound

HRID 527919Notes

Reaction equation

HRID 527919 reaction equation
CN[C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]3[CH:16]=[CH:15][NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH2:4]1.[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1F)[C:21]#[N:22].C[CH2:28][N:29](C(C)C)C(C)C.O>CS(C)=O>[N:11]1[C:10]2[NH:14][CH:15]=[CH:16][C:9]=2[C:8]([N:5]2[CH2:6][CH2:7][CH:3]([C:25]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([NH:29][CH3:28])[C:18]=3[F:17])[CH2:4]2)=[N:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 5872033,4-DifluorobenzonitrileHCID 68027120HCID 68027120, compound

Product 1

HCID 86692143HCID 86692143, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (R)—N-methyl-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-amine (0.50 g, 2.3 mmol), 3,4-difluorobenzonitrile (0.48 g, 3.45 mmol) and DIPEA (0.59 g, 4.6 mmol) in DMSO (10 mL) was stirred at 90° C. for overnight. The mixture was poured into water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined extracts was washed with brine (2×50 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography to give the title compound (0.404 g, 52% yield). MS (m/z): 337 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe combined extracts was washed with brine (2×50 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-d7f281e733aa4b40b8fbc3e395778a9b
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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