Methanesulfonyl chloride → HCID 58748241, compound

HRID 1162710Notes

Reaction equation

HRID 1162710 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])[CH:5]=[CH:4][C:3]=1[NH:15][C:16]([N:18]1[CH2:22][CH:21]([NH:23][CH3:24])[C@H:20]([CH2:25][NH:26][C:27]([C:29]2[S:30][C:31]([Cl:34])=[CH:32][CH:33]=2)=[O:28])[CH2:19]1)=[O:17].[CH3:35][S:36](Cl)(=[O:38])=[O:37]>CC#N.C(N(CC)C(C)C)(C)C.CO>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])[CH:5]=[CH:4][C:3]=1[NH:15][C:16]([N:18]1[CH2:22][CH:21]([N:23]([S:36]([CH3:35])(=[O:38])=[O:37])[CH3:24])[C@H:20]([CH2:25][NH:26][C:27]([C:29]2[S:30][C:31]([Cl:34])=[CH:32][CH:33]=2)=[O:28])[CH2:19]1)=[O:17]

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 58748218HCID 58748218, compound

Product 1

HCID 58748241HCID 58748241, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of (R)-3-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-4-methylamino-pyrrolidine-1-carboxylic acid[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenyl]-amide (example 83; 26 mg) in 0.8 ml of CH3CN and 22 μl of N,N-diisopropylethylamine was added at 22° C. 6 μl of methanesulfonylchloride and stirring was continued for 3 h. The mixture was diluted with 0.5 ml of MeOH, evaporated and the residue was chromatographed on silica (AcOEt/MeOH, 15:1) to give (R)-3-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-4-(methanesulfonyl-methyl-amino)-pyrrolidine-1-carboxylic acid[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenyl]-amide. Colorless solid. MS 582.0 ([M+H]+)

Workup

  1. customevaporated
  2. customthe residue was chromatographed on silica (AcOEt/MeOH, 15:1)

Sources & evidence

ORD record
ord-2e05ba14c9dc476e8fd24940581736cc
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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