Pyridine → HCID 67999349, compound

HRID 1048404Notes

Reaction equation

HRID 1048404 reaction equation
[CH2:1]([C@@:4]1([CH3:35])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:32][CH3:33])[CH2:25][NH:26][CH2:27][C:28]([F:31])([F:30])[F:29])[C:5]1=[O:34])[CH:2]=[CH2:3].[CH3:36][S:37](Cl)(=[O:39])=[O:38].N1C=CC=CC=1>ClCCCl.CN(C1C=CN=CC=1)C>[CH2:1]([C@@:4]1([CH3:35])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:32][CH3:33])[CH2:25][N:26]([CH2:27][C:28]([F:29])([F:31])[F:30])[S:37]([CH3:36])(=[O:39])=[O:38])[C:5]1=[O:34])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chloride2×HCID 68000385HCID 68000385, compound

Product 1

HCID 67999349HCID 67999349, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-1-((S)-1-(2,2,2-trifluoroethylamino)butan-2-yl)piperidin-2-one prepared above in Step A (60.9 mg, 0.115 mmol) in DCE (770 μL) was added DMAP (70.5 mg, 0.577 mmol) and methanesulfonyl chloride (35.9 μL, 0.462 mmol) successively at rt. After being stirred at rt for 3 h, pyridine (46.7 μL, 0.577 mmol), methanesulfonyl chloride (35.9 μL, 0.462 mmol), and DCE (0.77 mL) were added and the resulting solution was stirred for 15 h.

Workup

  1. stirringthe resulting solution was stirred for 15 h.

Sources & evidence

ORD record
ord-00ade85ce5e841d9ba9b0dd7a24afc38
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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