3-Pyridinemethanamine → 4-[4-(4-Fluoro-phenyl)-piperidin-1-yl]-2-[(pyridin-3-ylmethyl)-amino]-6-(2,2,2-trifluoro-ethoxy)-pyrimidine-5-carbonitrile
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]3[C:19]([C:20]#[N:21])=[C:18]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])[N:17]=[C:16](SC)[N:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=O)C=1.FC1C=CC(C2CCN(C3C(C#N)=C(OCC(F)(F)F)N=C(S(C)(=O)=O)N=3)CC2)=CC=1.[N:72]1[CH:77]=[CH:76][CH:75]=[C:74]([CH2:78][NH2:79])[CH:73]=1>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]3[C:19]([C:20]#[N:21])=[C:18]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])[N:17]=[C:16]([NH:79][CH2:78][C:74]4[CH:73]=[N:72][CH:77]=[CH:76][CH:75]=4)[N:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1Participants
6
Reactant 4
HCID 310183-Pyridinemethanamine
HCID 70297m-Chloroperbenzoic acid
HCID 187531954-[4-(4-Fluoro-phenyl)-piperidin-1-yl]-2-methanesulfonyl-6-(2,2,2-trifluoro-ethoxy)-pyrimidine-5-carbonitrile
HCID 187532314-[4-(4-Fluoro-phenyl)-piperidin-1-yl]-2-methylsulfanyl-6-(2,2,2-trifluoro-ethoxy)-pyrimidine-5-carbonitrileProduct 1
Reagents, catalysts & solvents 1
Procedure
In analogy to the procedure described in example 57c, the 4-[4-(4-fluoro-phenyl)-piperidin-1-yl]-2-methylsulfanyl-6-(2,2,2-trifluoro-ethoxy)-pyrimidine-5-carbonitrile was oxidized by 3-chloro-perbenzoic acid to 4-[4-(4-fluoro-phenyl)-piperidin-1-yl]-2-methanesulfonyl-6-(2,2,2-trifluoro-ethoxy)-pyrimidine-5-carbonitrile which was then treated with 3-picolylamine in dioxane at 40° C. during 18 hours to yield the 4-[4-(4-fluoro-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]+=487.
Sources & evidence
- ORD record
- ord-0fada72fbc36403fbbc6f8b033d821df
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06673795B2
Reaction notes
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