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

HRID 2217884Notes

Reaction equation

HRID 2217884 reaction equation
[Cl:1][C:2]1[C:3]([NH:19][C:20](=[O:28])[CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([OH:18])[CH2:13]1)[CH:6]=[CH:5]2.C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>ClCCl>[Cl:1][C:2]1[C:3]([NH:19][C:20](=[O:28])[CH2:21][CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([O:18][S:37]([CH3:36])(=[O:39])=[O:38])[CH2:13]1)[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11258141N-[6-Chloro-2-[(3R)-3-hydroxy-1-piperidinyl]-5-quinolinyl]-cyclohexaneacetamide

Product 1

HCID 86609747N-[6-Chloro-2-[(3R)-3-[(methylsulfonyl)oxy]-1-piperidinyl]-5-quinolinyl]cyclohexaneacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-[6-chloro-2-[(3R)-3-hydroxy-1-piperidinyl]-5-quinolinyl]-cyclohexaneacetamide (Example 37) (0.715 g) in dichloromethane (10 mL) was added triethylamine (0.99 mL) followed by methanesulfonyl chloride (0.275 mL). The reaction was stirred under nitrogen for 24 hours followed by the removal of volatiles under vacuum. The resulting mixture was taken up in methanol (20 mL) and placed down a Varian® SCX cartridge, washed with methanol (50 mL) and eluted with ammonia in methanol (0.7M, 50 mL). The solvent was removed to afford the sub-titled compound (0.64 g).

Workup

  1. customfollowed by the removal of volatiles under vacuum
  2. washwashed with methanol (50 mL)
  3. washeluted with ammonia in methanol (0.7M, 50 mL)
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-5f7755e9e1de4df8b4b6cac9c10b3e8c
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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