(4-Methoxycyclohexyl)methyl trifluoromethanesulphonate → tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(4-methoxycyclohexyl)propanoate

HRID 56896Notes

Reaction equation

HRID 56896 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:25]#[N:26])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:10](=[O:24])[CH:9]=2)[CH:7]=1.FC(F)(F)S(O[CH2:33][CH:34]1[CH2:39][CH2:38][CH:37]([O:40][CH3:41])[CH2:36][CH2:35]1)(=O)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:25]#[N:26])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:33][CH:34]3[CH2:39][CH2:38][CH:37]([O:40][CH3:41])[CH2:36][CH2:35]3)[C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C:10](=[O:24])[CH:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 117605726(4-Methoxycyclohexyl)methyl trifluoromethanesulphonateHCID 117622654tert-Butyl [4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate

Product 1

HCID 117622768tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(4-methoxycyclohexyl)propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.40 g (14.4 mmol) of tert-butyl [4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate, 5.97 g (21.6 mmol) of (4-methoxycyclohexyl)methyl trifluoromethanesulphonate (cis/trans isomer mixture) and 15.8 ml (15.8 mmol) of bis(trimethylsilyl)lithium amide (1M in THF) in 114 ml of THF were reacted according to General Method 7B. Yield: 10.8 g (purity 51%) of crude product

Sources & evidence

ORD record
ord-65eca40aada746de95086644c861ddc6
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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