Methanesulfonyl chloride → (5-bromo-2-methylsulfanyl-pyrimidin-4-yl)-((S)-1-methanesulfonyl-piperidin-3-yl)-amine

HRID 1916116Notes

Reaction equation

HRID 1916116 reaction equation
[Br:1][C:2]1[C:3]([NH:10][C@H:11]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]2)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[Br:1][C:2]1[C:3]([NH:10][C@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([S:27]([CH3:26])(=[O:29])=[O:28])[CH2:12]2)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58177241(5-bromo-2-methylsulfanyl-pyrimidin-4-yl)-(S)-piperidin-3-yl-amine

Product 1

HCID 69811702(5-bromo-2-methylsulfanyl-pyrimidin-4-yl)-((S)-1-methanesulfonyl-piperidin-3-yl)-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (5-bromo-2-methylsulfanyl-pyrimidin-4-yl)-(S)-piperidin-3-yl-amine (2.9 g, 9.6 mmol) and diisopropylethylamine (3.7 g, 28 mmol) in dichloromethane (50 ml) was cooled to 5° C. and treated with a solution of methanesulfonyl chloride (1.21 g, 10.5 mmol) in dichloromethane (20 ml). This was stirred at room temperature for 14 hours, washed with water, dried (MgSO4) and evaporated to give (5-bromo-2-methylsulfanyl-pyrimidin-4-yl)-((S)-1-methanesulfonyl-piperidin-3-yl)-amine as a white solid. MS (ES+): 382 (2602-33).

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-68d69e4bfd364bae92768638200bfa15
Source dataset
uspto-grants-2013_12
Patent number
US08618103B2

Reaction notes

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