3-Fluorobenzenesulfonyl Chloride → HCID 69317589, compound

HRID 2114611Notes

Reaction equation

HRID 2114611 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[CH:12][N:13]=[C:14]([NH2:15])[C:9]=3[C:8]([C:16]3[NH:20][C:19]4[CH:21]=[C:22]([N+:25]([O-])=O)[CH:23]=[CH:24][C:18]=4[N:17]=3)=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:28][C:29]1[CH:30]=[C:31]([S:35](Cl)(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1>CS(C)=O>[NH2:15][C:14]1[C:9]2[C:8]([C:16]3[NH:20][C:19]4[CH:21]=[C:22]([NH:25][S:35]([C:31]5[CH:32]=[CH:33][CH:34]=[C:29]([F:28])[CH:30]=5)(=[O:37])=[O:36])[CH:23]=[CH:24][C:18]=4[N:17]=3)=[CH:7][N:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[C:10]=2[N:11]=[CH:12][N:13]=1

Participants

4

Reactant 2

HCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 69320502HCID 69320502, compound

Product 1

HCID 69317589HCID 69317589, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared by treatment of 5-(6-Amino-1H-benzoimidazol-2-yl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (1E, 20 mg in 1.0 mL NMP) with 1.2 equiv. of 3-fluoro-benzenesulfonyl chloride (14.3 mg) at 80° C. for 2.5 h. LCMS was used to confirm product formation and the resulting reaction mixture was diluted with 1.0 mL DMSO and purified via preparative HPLC to furnish the desired product (M/Z 491.2, retention time 2.3 min. with analytical HPLC method 2).

Workup

  1. customthe resulting reaction mixture
  2. custompurified via preparative HPLC

Sources & evidence

ORD record
ord-39018f5132b94d84a3ceb109ed094aa9
Source dataset
uspto-grants-2008_10
Patent number
US07435739B2

Reaction notes

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