Methanesulfonyl chloride → N-{5-[4-(2-(S)-Pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-phenyl]-pyridin-2-yl}-methanesulfonamide

HRID 1867806Notes

Reaction equation

HRID 1867806 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][C@H:17]3[CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl.N1C=CC=CC=1>[N:22]1([CH2:21][C@@H:17]2[CH2:18][CH2:19][CH2:20][N:16]2[C:14]([C:11]2[CH:10]=[CH:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:28]([CH3:27])(=[O:30])=[O:29])=[N:7][CH:6]=3)=[CH:13][CH:12]=2)=[O:15])[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 57980103[4-(6-Amino-pyridin-3-yl)-phenyl]-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

Product 1

HCID 57980066N-{5-[4-(2-(S)-Pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-phenyl]-pyridin-2-yl}-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 21875418Pyridine methylene chlorideSolvent

Procedure

Procedure LL: To a stirring solution of [4-(6-amino-pyridin-3-yl)-phenyl]-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone (1.0 mmol) in 3:1 dichloromethane/pyridine (0.10M), add methanesulfonyl chloride (1.3 mmol) and stir at room temperature for 48 hours. After this time, wash the reaction with 1N hydrochloric acid while extracting with dichloromethane. Using 2N sodium hydroxide, make the aqueous phase basic and extract with 10% isopropanol/dichloromethane. The product remains in the aqueous layer during the acid/base workup. Concentrate the aqueous layer in vacuo and purify the title compound via radial chromatography eluting with 2M ammonia and dichloromethane. MS (m/e): 429.2 (M+1)

Workup

  1. washAfter this time, wash
  2. customthe reaction with 1N hydrochloric acid
  3. extractionwhile extracting with dichloromethane
  4. extractionextract with 10% isopropanol/dichloromethane
  5. concentrationConcentrate the aqueous layer in vacuo
  6. custompurify the title compound via radial chromatography
  7. washeluting with 2M ammonia and dichloromethane

Sources & evidence

ORD record
ord-55982b0734a24f7381420dfca74d23da
Source dataset
uspto-grants-2009_12
Patent number
US07632857B2

Reaction notes

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