Diisopropylethylamine → (5-bromo-2-methylsulfanyl-pyrimidin-4-yl)-[(S)-1-(2-methyl-propane-1-sulfonyl)-piperidin-3-yl]-amine

HRID 1916119Notes

Reaction equation

HRID 1916119 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][CH:27]([CH3:33])[CH2:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl>[Br:1][C:2]1[C:3]([NH:10][C@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([S:29]([CH2:28][CH:27]([CH3:33])[CH3:26])(=[O:31])=[O:30])[CH2:12]2)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1822361-Propanesulfonyl chloride, 2-methyl-HCID 58177241(5-bromo-2-methylsulfanyl-pyrimidin-4-yl)-(S)-piperidin-3-yl-amine

Product 1

HCID 69812744(5-bromo-2-methylsulfanyl-pyrimidin-4-yl)-[(S)-1-(2-methyl-propane-1-sulfonyl)-piperidin-3-yl]-amineYield 71.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (5-bromo-2-methylsulfanyl-pyrimidin-4-yl)-(S)-piperidin-3-yl-amine (1.0 g, 3.3 mmol) from Scheme 1, step 1, Example 76 and diisopropylethylamine (1.6 ml, 6.6 mmol) in dichloromethane (15 ml) was cooled to 5° C. and treated with a solution of 2-methylpropane-1-sulfonyl chloride (0.52 g, 3.3 mmol) in dichloromethane (2 ml) similar to step 2. This was stirred at room temperature for 16 hours, washed with water, dried (MgSO4) and evaporated to give an oil. This was purified by silica gel chromatography (50-80% ethyl acetate/hexane) to give 1.0 g (65%) (5-bromo-2-methylsulfanyl-pyrimidin-4-yl)-[(S)-1-(2-methyl-propane-1-sulfonyl)-piperidin-3-yl]-amine. MS (ES+): 424

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customto give an oil
  5. customThis was purified by silica gel chromatography (50-80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-10540688b7a846b69c01f52dcc669c49
Source dataset
uspto-grants-2013_12
Patent number
US08618103B2

Reaction notes

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