Methanesulfonyl chloride → N-[4-(4-Chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenyl]-methanesulfonamide

HRID 629009Notes

Reaction equation

HRID 629009 reaction equation
[Cl:1][C:2]1[C:7]([S:8][CH3:9])=[C:6]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)[N:3]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[Cl:1][C:2]1[C:7]([S:8][CH3:9])=[C:6]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][S:24]([CH3:23])(=[O:26])=[O:25])=[CH:18][CH:17]=2)[N:3]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86673495HCID 86673495, compound

Product 1

HCID 86673496N-[4-(4-Chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenyl]-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(4-chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenylamine (30 mg, 0.091 mmol.), methanesulfonyl chloride (15.5 mg, 0.136 mmol, 1.5 eq.) and CH2Cl2 was added to the reaction vessel and flushed with argon. The reaction mixture was stirred at r.t. for 2 hrs. The reaction mixture was partitioned between CH2Cl2 and NaHCO3 (aq), the organic layer was washed with brine, dried over MgSO4, filtered and evaporated in vacuo. A white solid of 30.3 mg (82.1%) was obtained as the product.

Workup

  1. additionwas added to the reaction vessel
  2. customflushed with argon
  3. customThe reaction mixture was partitioned between CH2Cl2 and NaHCO3 (aq)
  4. washthe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customA white solid of 30.3 mg (82.1%) was obtained as the product

Sources & evidence

ORD record
ord-69b170ead6e84c82943c147b07956a80
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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