Pyridine → HCID 67999349, compound

HRID 932091Notes

Reaction equation

HRID 932091 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-8456457d44ac43d884a1c8c9ed177029
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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