1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine → 5-phenyl-4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one

HRID 1518474Notes

Reaction equation

HRID 1518474 reaction equation
[OH:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][NH:5][C:4](=[O:14])[CH:3]=1.CS(C1C=CNC(=O)C=1)(=O)=O.[CH2:26]([C:29]1[CH:30]=[N:31][C:32]([N:35]2[CH2:40][CH2:39][CH:38](CS([O-])(=O)=O)[CH2:37][CH2:36]2)=[N:33][CH:34]=1)[CH2:27][CH3:28].CS(OC1CCN(C(OC(C)(C)C)=O)CC1)(=O)=O>>[C:8]1([C:7]2[C:2]([O:1][CH:38]3[CH2:39][CH2:40][N:35]([C:32]4[N:31]=[CH:30][C:29]([CH2:26][CH2:27][CH3:28])=[CH:34][N:33]=4)[CH2:36][CH2:37]3)=[CH:3][C:4](=[O:14])[NH:5][CH:6]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 546832584-Hydroxy-5-phenylpyridin-2(1H)-oneHCID 552965804-(Methylsulfonyl)pyridin-2(1H)-oneHCID 866580301-(5-Propylpyrimidin-2-yl)piperidin-4-ylmethanesulfonate

Product 1

HCID 673696175-phenyl-4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one

Procedure

The compound in Step C was prepared according to the procedures described in Example 1 substituting 4-hydroxy-5-phenylpyridin-2(1H)-one for 4-hydroxy-1-(4-(methylsulfonyl)pyridine-2(1H)-one and 1-(5-propylpyrimidin-2-yl)piperidin-4-ylmethanesulfonate for tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate in Step D. MS (ESI) 391 (M+H).

Workup

  1. customThe compound in Step C was prepared

Sources & evidence

ORD record
ord-891e42d742194eec90dd1d4e0d339f2c
Source dataset
uspto-grants-2012_07
Patent number
US08232404B2

Reaction notes

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