Methanesulfonyl chloride → HCID 57942459, compound

HRID 419174Notes

Reaction equation

HRID 419174 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([C:10]2[C:15]([N:16](COC)[S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:21]=3)(=[O:19])=[O:18])=[CH:14][C:13]([Cl:34])=[CH:12][N:11]=2)=[O:9])[CH:5]=[CH:4][N:3]=1.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>N1C=CC=CC=1>[Cl:34][C:13]1[CH:14]=[C:15]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:21]=2)(=[O:19])=[O:18])[C:10]([C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:1][S:36]([CH3:35])(=[O:38])=[O:37])[CH:7]=2)=[O:9])=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 57942452HCID 57942452, compound

Product 1

HCID 57942459HCID 57942459, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-[2-(2-amino-pyridine-4-carbonyl)-5-chloro-pyridin-3-yl]-N-methoxymethyl-4-methyl-3-trifluoromethyl-benzenesulfonamide (140 mg, 0.272 mmol) in pyridine (0.75 mL) was added methanesulfonyl chloride (0.042 mL, 0.544 mmol). The reaction was warmed to 50° C. and stirred 2.5 h. The resultant mixture was quenched with 10% HCl, diluted with EtOAc, and the organic layer washed with 10% HCl and saturated sodium bicarbonate. The combined organics were dried with sodium sulfate, concentrated in vacuo, and purified via automated silica gel chromatography to produce the desired sulfonamide.

Workup

  1. customThe resultant mixture was quenched with 10% HCl
  2. additiondiluted with EtOAc
  3. washthe organic layer washed with 10% HCl and saturated sodium bicarbonate
  4. dry with materialThe combined organics were dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified

Sources & evidence

ORD record
ord-f638bd7807534aa393dc61df4e892b75
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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