Ethanolamine → HCID 10136967, compound

HRID 1838192Notes

Reaction equation

HRID 1838192 reaction equation
CS[C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)[C:6]([C:21]#[N:22])=[C:5]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])[N:4]=1.ClC1C=CC=C(C(OO)=O)C=1.CS(C1N=C(N2CCC(C3C=CC=CC=3)CC2)C(C#N)=C(OCC(F)(F)F)N=1)(=O)=O.[CH2:70]([CH2:72][NH2:73])[OH:71]>O1CCOCC1>[OH:71][CH2:70][CH2:72][NH:73][C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:11][CH2:10]2)[C:6]([C:21]#[N:22])=[C:5]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])[N:4]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 70297m-Chloroperbenzoic acidHCID 18753203HCID 18753203, compoundHCID 18753241HCID 18753241, compound

Product 1

HCID 10136967HCID 10136967, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In analogy to the procedure described in example 57c, 2-methylsulfanyl-4-(4-phenyl-piperidin-1-yl)-6-(2,2,2-trifluoro-ethoxy)-pyrimidine-5-carbonitrile was oxidized by 3-chloro-perbenzoic acid to 2-methanesulfonyl-4-(4-phenyl-piperidin-1-yl)-6-(2,2,2-trifluoro-ethoxy)-pyrimidine-5-carbonitrile which was then treated in crude form with ethanolamine in dioxane at 40° C. during 18 hours to yield the 2-(2-hydroxy-ethylamino)-4-(4-phenyl-piperidin-1-yl)-6-(2,2,2-trifluoro-ethoxy)-pyrimidine-5-carbonitrile as an amorphous, white solid; MS: [M+H]+=422.

Sources & evidence

ORD record
ord-1c2976bba26e407ab01fe1e2b16218af
Source dataset
uspto-grants-2004_01
Patent number
US06673795B2

Reaction notes

Loading…