Triethylamine → HCID 21258216, compound

HRID 635214Notes

Reaction equation

HRID 635214 reaction equation
CS(Cl)(=O)=O.[Br:6][C:7]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:10]=[CH:9][C:8]=1[N:16]([C:19]1[N:24]=[C:23]([N:25]2[CH2:30][CH2:29][C:28]([C:32]3[O:33][CH:34]=[CH:35][CH:36]=3)(O)[CH2:27][CH2:26]2)[CH:22]=[C:21]([CH3:37])[N:20]=1)[CH2:17][CH3:18].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl.CN(C)C1C=CN=CC=1>[Br:6][C:7]1[CH:12]=[C:11]([CH:13]([CH3:14])[CH3:15])[CH:10]=[CH:9][C:8]=1[N:16]([C:19]1[N:24]=[C:23]([N:25]2[CH2:26][CH:27]=[C:28]([C:32]3[O:33][CH:34]=[CH:35][CH:36]=3)[CH2:29][CH2:30]2)[CH:22]=[C:21]([CH3:37])[N:20]=1)[CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 21258205HCID 21258205, compound

Product 1

HCID 21258216HCID 21258216, compoundYield 69.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 48 mg of methanesulfonyl chloride in 0.5 ml of dichloromethane was added dropwise under ice-cooling to a solution of 104 mg of 2-[N-(2-bromo-4-isopropylphenyl)-N-ethylamino]-4-[4-(furan-2-yl)-4-hydroxypiperidin-1-yl]-6-methylpyrimidine, 85 mg of triethylamine, and 13 mg of 4-dimethylaminopyridine in 1 ml of dichloromethane, followed by stirring for 15 minutes and then at room temperature for 2 hours. The reaction solution was poured into a saturated sodium hydrogencarbonate aqueous solution and extracted with ethyl acetate. The extract was washed successively with a saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The desiccant was filtered off, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=9/1) to give 70 mg of 2-[N-(2-bromo-4-isopropylphenyl)-N-ethylamino]-4-[4-(furan-2-yl)-1,2,3,6-tetrahydropyridin-1-yl]-6-methylpyrimidine.

Workup

  1. waitat room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed successively with a saturated sodium hydrogencarbonate aqueous solution
  4. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate
  5. filtrationThe desiccant was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-308b71d3d3cc49f6a0de82da553ce9c6
Source dataset
uspto-grants-2001_02
Patent number
US06187781B1

Reaction notes

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