Methanesulfonyl chloride → HCID 67396174, compound

HRID 1426720Notes

Reaction equation

HRID 1426720 reaction equation
[F:1][C:2]1[C:3]([CH2:25][N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:4][N:5]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23]O)[CH:18]=2)(=[O:16])=[O:15])[C:6]=1[C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1.CS([Cl:39])(=O)=O.C(N(C(C)C)CC)(C)C>O1CCCC1>[Cl:39][CH2:23][C:19]1[CH:18]=[C:17]([S:14]([N:5]2[C:6]([C:7]3[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=3)=[C:2]([F:1])[C:3]([CH2:25][N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:4]2)(=[O:16])=[O:15])[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67399475HCID 67399475, compound

Product 1

HCID 67396174HCID 67396174, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl [(4-fluoro-5-(2-fluoropyridin-3-yl)-1-{[3-(hydroxymethyl)phenyl]sulfonyl}-1H-pyrrol-3-yl)methyl]methylcarbamate (683 mg) in tetrahydrofuran (5 mL) were added methanesulfonyl chloride (174 mg) and diisopropylethylamine (215 mg) under ice-cooling, and the mixture was stirred at room temperature for 60 hr. The solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→3:1) to give the title compound as a pale-yellow oil (yield 386 mg, 55%).

Workup

  1. temperaturecooling
  2. concentrationThe solvent was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→3:1)

Sources & evidence

ORD record
ord-cd15dc2eda5c4f16b25d019398dfe8fa
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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