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 1518496Notes

Reaction equation

HRID 1518496 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=CNC(=O)C=1.CS(O[CH:32]1[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]1)(=O)=O.CS(OC1CCN(C2N=CC(CCC)=CN=2)CC1)(=O)=O>>[Cl:1][C:2]1[C:3]([O:18][CH:32]2[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]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 546960044-Hydroxy-2(1H)-pyridinoneHCID 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

Example 267 was prepared according to procedures described in Example 173 Step C substituting 4-(5-chloro-4-hydroxy-2-oxopyridin-1(2H)-yl)-2-fluorobenzonitrile (prepared according to the procedure described in Step B of Example 263) for 4-hydroxypyridin-2(1H)-one and substituting tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (prepared according to the procedure described in Step C of Example 1) for 1-(5-propylpyrimidin-2-yl)piperidin-4-yl methanesulfonate except that the crude product was purified by flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2). 1H NMR (400 MHz, CDCl3) δ ppm 7.77 (t, J=7.53 Hz, 1 H), 7.37-7.46 (m, 2 H), 7.30-7.36 (m, 1 H), 6.00 (s, 1 H), 4.54-4.68 (m, 1 H), 3.58-3.71 (m, 2 H), 3.40-3.56 (m, 2 H), 1.93-2.07 (m, 2 H), 1.78-1.93 (m, 2 H), 1.49 (s, 9 H). MS (ESI) 392 (M−56+H).

Workup

  1. customExample 267 was prepared
  2. customprepared
  3. customprepared
  4. customwas purified by flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-d3a5016065a34804b16132dd0b4af20e
Source dataset
uspto-grants-2012_07
Patent number
US08232404B2

Reaction notes

Loading…