4-Cyanobenzenesulfonyl chloride → HCID 56837010, compound

HRID 527911Notes

Reaction equation

HRID 527911 reaction equation
[CH3:1][NH:2][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.[C:17]([C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1)#[N:18].CCN(C(C)C)C(C)C>C1COCC1.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][C@@H:3]([N:2]([CH3:1])[S:25]([C:22]3[CH:21]=[CH:20][C:19]([C:17]#[N:18])=[CH:24][CH:23]=3)(=[O:27])=[O:26])[CH2:4]2)=[N:13][CH:12]=1

Participants

6

Reactant 3

HCID 394974-Cyanobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68027120HCID 68027120, compound

Product 1

HCID 56837010HCID 56837010, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)—N-methyl-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-amine (30 mg, 0.138 mmol) in THF (2 mL) were added 4-cyanobenzene-1-sulfonyl chloride (42 mg, 0.208 mmol) and DIPEA (36 mg, 0.28 mmol). The reaction mixture was stirred at room temperature for 0.5 hour. The reaction mixture was then diluted with water, and extracted with EtOAc. The organic layers were combined, dried, and concentrated. The residue was purified by preparative TLC to give the title compound (13.6 mg, 26%). MS (m/z): 383 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-0841da6736134012a62e162d6b3a4074
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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