3-Pyridinemethanamine → HCID 10226976, compound

HRID 1838191Notes

Reaction equation

HRID 1838191 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.[N:70]1[CH:75]=[CH:74][CH:73]=[C:72]([CH2:76][NH2:77])[CH:71]=1>O1CCOCC1>[C:15]1([CH:12]2[CH2:13][CH2:14][N:9]([C:7]3[C:6]([C:21]#[N:22])=[C:5]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])[N:4]=[C:3]([NH:77][CH2:76][C:72]4[CH:71]=[N:70][CH:75]=[CH:74][CH:73]=4)[N:8]=3)[CH2:10][CH2:11]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 310183-PyridinemethanamineHCID 70297m-Chloroperbenzoic acidHCID 18753203HCID 18753203, compoundHCID 18753241HCID 18753241, compound

Product 1

HCID 10226976HCID 10226976, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In analogy to the procedure described in example 57c, the 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 the 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 3-picolylamine in dioxane at 40° C. during 18 hours to yield the 4-(4-phenyl-piperidin-1-yl)-2-[(pyridin-3-ylmethyl)-amino]-6-(2,2,2-trifluoro-ethoxy)-pyrimidine-5-carbonitrile as an amorphous, light brown solid; MS: [M+H]+=469.

Sources & evidence

ORD record
ord-496c542dd4b548f68c0f1e378a9d6d9e
Source dataset
uspto-grants-2004_01
Patent number
US06673795B2

Reaction notes

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