Triethylamine → HCID 178505321, compound

HRID 1160262Notes

Reaction equation

HRID 1160262 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([N:31]3[CH2:36][CH2:35][CH:34]([C:37]([F:40])([F:39])[F:38])[CH2:33][CH2:32]3)=[O:30])=[CH:25][CH:24]=2)[CH:5]=[C:6]([Cl:22])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]2)[C:10]1=[O:21].C(N(CC)CC)C.[CH3:48][S:49](Cl)(=[O:51])=[O:50]>ClCCl>[Cl:22][C:6]1[CH:5]=[C:4]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([N:31]3[CH2:36][CH2:35][CH:34]([C:37]([F:38])([F:40])[F:39])[CH2:33][CH2:32]3)=[O:30])=[CH:25][CH:24]=2)[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([O:20][S:49]([CH3:48])(=[O:51])=[O:50])[CH2:16][CH2:15]2)[C:10]1=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178519417HCID 178519417, compound

Product 1

HCID 178505321HCID 178505321, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve (R)-3-[3,5-Dichloro-4′-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-trans-1-(4-hydroxy-cyclohexyl)-pyrrolidin-2-one (Preparation 23) (0.419 g, 0.70 mmol) in 10 ml of dry dichloromethane at 0° C. Add triethylamine (0.18 ml, 1.41 mmol) followed by methanesulfonyl chloride (0.06 ml, 0.77 mmol). Stir at room temperature for 5 hours. Quench with 1N HCl and extract with ethyl acetate. Wash the extract with 1N HCl, NaHCO3 and brine. Dry over magnesium sulfate, filter, and concentrate. Filter through a short silica plug to receive 0.45 g (95%) of the title compound: Mass spectrum (apci) m/z=675 (M+H).

Workup

  1. customQuench with 1N HCl
  2. extractionextract with ethyl acetate
  3. washWash the
  4. extractionextract with 1N HCl, NaHCO3 and brine
  5. dry with materialDry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. filtrationFilter through a short silica plug

Sources & evidence

ORD record
ord-ac0474052a094b0ca58961e2e9be00c5
Source dataset
uspto-grants-2010_10
Patent number
US07816349B2

Reaction notes

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