4-Amino-6-{4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbonitrile → 4-Amino-6-{4-[1-(2-azetidin-1-yl-ethyl)-4-(4-difluoromethoxy-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbonitrile

HRID 2284001Notes

Reaction equation

HRID 2284001 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6](N2CCC(C3N(C)C=C(C4C=CC(F)=C(C(F)(F)F)C=4)N=3)CC2)[N:5]=[CH:4][N:3]=1.FC(F)(F)C(O)=O.[N:40]1([CH2:44][CH2:45][N:46]2[CH:50]=[C:49]([C:51]3[CH:56]=[CH:55][C:54]([O:57][CH:58]([F:60])[F:59])=[CH:53][CH:52]=3)[N:48]=[C:47]2[CH:61]2[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]2)[CH2:43][CH2:42][CH2:41]1>>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([N:64]2[CH2:63][CH2:62][CH:61]([C:47]3[N:46]([CH2:45][CH2:44][N:40]4[CH2:43][CH2:42][CH2:41]4)[CH:50]=[C:49]([C:51]4[CH:52]=[CH:53][C:54]([O:57][CH:58]([F:60])[F:59])=[CH:55][CH:56]=4)[N:48]=3)[CH2:66][CH2:65]2)[N:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 894424644-Amino-6-{4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbonitrileHCID 894428564-[1-(2-Azetidin-1-yl-ethyl)-4-(4-difluoromethoxy-phenyl)-1H-imidazol-2-yl]-piperidine trifluoroacetate

Product 1

HCID 1177008014-Amino-6-{4-[1-(2-azetidin-1-yl-ethyl)-4-(4-difluoromethoxy-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbonitrile

Procedure

The title compound was prepared in an analogous manner as 4-amino-6-{4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbonitrile using 4-[1-(2-Azetidin-1-yl-ethyl)-4-(4-difluoromethoxy-phenyl)-1H-imidazol-2-yl]-piperidine trifluoroacetate instead of 4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-methyl-1h-imidazol-2-yl]-piperidine. LC-MS: (M+1=495, obsd.=495).

Sources & evidence

ORD record
ord-a336d2a0270b405c947620f5918cf045
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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