Dicyclohexylcarbodiimide → 2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorophenyl 3-[piperidino(carbonyl)]propionate

HRID 1722967

Reaction equation

HRID 1722967 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[C:4]([F:22])[CH:3]=1.[N:23]1([C:29]([CH2:31][CH2:32][C:33](O)=[O:34])=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[N:23]1([C:29]([CH2:31][CH2:32][C:33]([O:8][C:7]2[CH:6]=[C:5]([N:9]3[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:17])[F:19])[N:11]([CH3:20])[C:10]3=[O:21])[C:4]([F:22])=[CH:3][C:2]=2[Cl:1])=[O:34])=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 7928604-Oxo-4-(piperidin-1-yl)butanoic acidHCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 200261272-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorophenyl 3-[piperidino(carbonyl)]propionate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

using 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione and 3-[piperidino(carbonyl)]-propionic acid with N,N'-dicyclohexylcarbodiimide and 4-dimethylaminopyridine as the catalyst in methylene chloride there is obtained 2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4 -fluorophenyl 3-[piperidino(carbonyl)]propionate. 1H-NMR (CDC3, 400 MHz): 7.35 ppm (d,1H), 7.20 ppm (d,1H), 6.36 ppm (s,1H), 3.50-3.60 ppm (m,5H), 3.42 ppm (t,2H). 2.94 ppm (t,2H), 2.74 ppm (t,2H), 1.49°-1.70 ppm (m.6H);

Sources & evidence

ORD record
ord-c971bb67cbf745db94b0145f78005d6a
Source dataset
uspto-grants-1989_08
Patent number
US04859229

Linked notes

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