Triethylamine → N-[6-Chloro-2-[(3S)-3-[(methylsulfonyl)oxy]-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide

HRID 2217828Notes

Reaction equation

HRID 2217828 reaction equation
[Cl:1][C:2]1[C:3]([NH:18][C:19](=[O:27])[CH2:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13]1)[CH:6]=[CH:5]2.[CH3:28][S:29](Cl)(=[O:31])=[O:30].C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[C:3]([NH:18][C:19](=[O:27])[CH2:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:16][CH2:15][C@H:14]([O:17][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:13]1)[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59768617N-[6-Chloro-2-[(3S)-3-hydroxy-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide

Product 1

HCID 86609739N-[6-Chloro-2-[(3S)-3-[(methylsulfonyl)oxy]-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-[6-chloro-2-[(3S)-3-hydroxy-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide (Example 29) (0.4 g) in dichloromethane was added methanesulphonyl chloride (0.104 mL) and triethylamine (0.215 mL). The reaction was stirred for 12 hours under nitrogen and then purified (Varian Chem elute cartridge, saturated sodium hydrogen carbonate solution and dichloromethane as eluant) to afford the sub-title compound (0.45 g).

Workup

  1. custompurified
  2. wash(Varian Chem elute cartridge, saturated sodium hydrogen carbonate solution and dichloromethane as eluant)

Sources & evidence

ORD record
ord-91f7f84cdf6c48ff888521a66c4b324c
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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