Methanesulfonyl chloride → HCID 57477613, compound

HRID 1501397Notes

Reaction equation

HRID 1501397 reaction equation
[CH3:1][C:2]([N:7]1[CH:11]=[C:10]([C:12]2[C:13]3[CH:20]=[CH:19][NH:18][C:14]=3[N:15]=[CH:16][N:17]=2)[CH:9]=[N:8]1)([CH3:6])[CH2:3][CH2:4][OH:5].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([O:5][CH2:4][CH2:3][C:2]([CH3:1])([N:7]1[CH:11]=[C:10]([C:12]2[C:13]3[CH:20]=[CH:19][NH:18][C:14]=3[N:15]=[CH:16][N:17]=2)[CH:9]=[N:8]1)[CH3:6])(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 574776123-Methyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butan-1-ol

Product 1

HCID 57477613HCID 57477613, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-methyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butan-1-ol (6.61 g, 0.0244 mol) in DCM (300 mL) at 0° C. was treated with TEA (3.74 mL, 0.0268 mol), followed by methanesulfonyl chloride (2.07 mL, 0.0268 mol). The reaction was stirred for 1 hour, and was then concentrated in vacuo. The crude residue was purified by flash column chromatography to afford the desired product (4.9 g, 57%).

Workup

  1. concentrationwas then concentrated in vacuo
  2. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-05b2aecea4a34e769033d13e5f6f934a
Source dataset
uspto-grants-2015_12
Patent number
US09206187B2

Reaction notes

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