1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine → Tert-butyl 4-(5-chloro-1-(4-cyano-3-fluorophenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

HRID 1895751Notes

Reaction equation

HRID 1895751 reaction equation
[Cl:1][C:2]1[C:3]([OH:18])=[CH:4][C:5](=[O:17])[N:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([F:16])[CH:9]=2)[CH:7]=1.OC1C(C#N)=CNC(=O)C=1.CS(O[CH:34]1[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]1)(=O)=O.CS(OC1CCN(C2N=CC(CCC)=CN=2)CC1)(=O)=O>>[Cl:1][C:2]1[C:3]([O:18][CH:34]2[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]2)=[CH:4][C:5](=[O:17])[N:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([F:16])[CH:9]=2)[CH:7]=1

Participants

5

Reactant 4

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 547063254,6-DihydroxynicotinonitrileHCID 673665324-(5-chloro-4-hydroxy-2-oxopyridin-1(2H)-yl)-2-fluorobenzonitrileHCID 866262675-Propylpyrimidin-2-ylpiperidin-4-yl methanesulfonate

Product 1

HCID 57468467Tert-butyl 4-(5-chloro-1-(4-cyano-3-fluorophenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

Procedure

The intermediate was prepared according to the procedures described in Example 221 substituting 4-(5-chloro-4-hydroxy-2-oxopyridin-1(2H)-yl)-2-fluorobenzonitrile for 4-hydroxy-6-oxo-1,6-dihydropyridine-3-carbonitrile and tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate for 1-(5-propylpyrimidin-2-yl)piperidin-4-yl methanesulfonate in Step B. MS (ESI) 392 (M+H).

Workup

  1. customThe intermediate was prepared

Sources & evidence

ORD record
ord-539738f1125c43ea973aae78dc6c3adc
Source dataset
uspto-grants-2013_08
Patent number
US08513424B2

Reaction notes

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