Triethylamine → HCID 59509060, compound

HRID 1020065Notes

Reaction equation

HRID 1020065 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([CH:18]2[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]2)=[O:17])[CH:10]=1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([CH:18]2[CH2:23][CH2:22][CH2:21][N:20]([S:32]([CH3:31])(=[O:34])=[O:33])[CH2:19]2)=[O:17])[CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 25227433HCID 25227433, compound

Product 1

HCID 59509060HCID 59509060, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Piperidine-3-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]-amide (compound #16A) (110 mg, 0.352 mmol) was dissolved in 5 mL of anhydrous dichloromethane, cooled to 0° C. and triethyl amine (13.0 g, 15.5 mmol) and methane sulfonyl chloride (60 mg, 0.53 mmol) were added simultaneously. The mixture was stirred for two hours at room temperature, treated with crushed ice and partitioned with between water and dichloromethane. The organic layer was separated, dried over sodium sulfate and concentrated to provide 1-methanesulfonyl-piperidine-3-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]-amide (compound #21A) (90 mg, 80.3%).

Workup

  1. additiontreated with crushed ice
  2. custompartitioned with between water and dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f3bdf80f66c9400d86be47665a113cf0
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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