Isopropylamine → 5-Ethoxy-6-{4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-(2-isopropylamino-ethyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-4-ylamine

HRID 2284099Notes

Reaction equation

HRID 2284099 reaction equation
NC1C(C#N)=C(N2CCC(C3N(CCNCC4CC4)[CH:18]=[C:19]([C:21]4C=CC(F)=C(C)C=4)[N:20]=3)CC2)N=CN=1.C(N)(C)C.[NH2:40][C:41]1[N:46]=[CH:45][N:44]=[C:43]([N:47]2[CH2:52][CH2:51][CH:50]([C:53]3[N:54]([CH2:69][CH2:70]OS(C)(=O)=O)[CH:55]=[C:56]([C:58]4[CH:63]=[CH:62][C:61]([F:64])=[C:60]([C:65]([F:68])([F:67])[F:66])[CH:59]=4)[N:57]=3)[CH2:49][CH2:48]2)[C:42]=1[O:76][CH2:77][CH3:78].NC1N=CN=C(N2CCC(C3N(CCOS(C)(=O)=O)C=C(C4C=CC(F)=C(C(F)(F)F)C=4)N=3)CC2)C=1C#N>>[CH2:77]([O:76][C:42]1[C:41]([NH2:40])=[N:46][CH:45]=[N:44][C:43]=1[N:47]1[CH2:52][CH2:51][CH:50]([C:53]2[N:54]([CH2:69][CH2:70][NH:20][CH:19]([CH3:21])[CH3:18])[CH:55]=[C:56]([C:58]3[CH:63]=[CH:62][C:61]([F:64])=[C:60]([C:65]([F:67])([F:66])[F:68])[CH:59]=3)[N:57]=2)[CH2:49][CH2:48]1)[CH3:78]

Participants

5

Reactant 4

HCID 6363IsopropylamineHCID 894426064-Amino-6-{4-[1-[2-(cyclopropylmethyl-amino)-ethyl]-4-(4-fluoro-3-methyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbonitrileHCID 89442673Methanesulfonic acid 2-[2-[1-(6-amino-5-cyano-pyrimidin-4-yl)-piperidin-4-yl]-4-(4-fluoro-3-trifluoromethyl-phenyl)-imidazol-1-yl]-ethyl esterHCID 89442808Methanesulfonic acid 2-[2-[1-(6-amino-5-ethoxy-pyrimidin-4-yl)-piperidin-4-yl]-4-(4-fluoro-3-trifluoromethyl-phenyl)-imidazol-1-yl]-ethyl ester

Product 1

HCID 715167645-Ethoxy-6-{4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-(2-isopropylamino-ethyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-4-ylamine

Procedure

The title compound was prepared in an analogous manner as 4-Amino-6-{4-[1-[2-(cyclopropylmethyl-amino)-ethyl]-4-(4-fluoro-3-methyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbonitrile using isopropylamine and methanesulfonic acid 2-[2-[1-(6-amino-5-ethoxy-pyrimidin-4-yl)-piperidin-4-yl]-4-(4-fluoro-3-trifluoromethyl-phenyl)-imidazol-1-yl]-ethyl ester instead of cyclopropylmethylamine and methanesulfonic acid 2-[2-[1-(6-amino-5-cyano-pyrimidin-4-yl)-piperidin-4-yl]-4-(4-fluoro-3-trifluoromethyl-phenyl)-imidazol-1-yl]ethyl ester. LC-MS: (M+1=536, obsd.=536).

Sources & evidence

ORD record
ord-a486bcfbcf254b26ace73fe831b83f11
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

Loading…