2,2,2-Trifluoro-1-[4-(4-{2-[3-(1-methyl-1H-pyrazol-4-yl)-phenyl]-pyrimidin-5-yl}-pyrazol-1-yl)-piperidin-1-yl]-ethanone → 4-[4-(4-{2-[3-(1-Methyl-1H-pyrazol-4-yl)-phenyl]-pyrimidin-5-yl}-pyrazol-1-yl)-cyclohexyl]-morpholin-3-one

HRID 1505715Notes

Reaction equation

HRID 1505715 reaction equation
FC(F)(F)C(N1CCC([N:11]2[CH:15]=[C:14]([C:16]3[CH:17]=[N:18][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]5[CH:29]=[N:30][N:31]([CH3:33])[CH:32]=5)[CH:23]=4)=[N:20][CH:21]=3)[CH:13]=[N:12]2)CC1)=O.IC1C=NN([C@H:42]2[CH2:47][CH2:46][C@H:45]([N:48]3[CH2:53][CH2:52][O:51][CH2:50][C:49]3=[O:54])[CH2:44][CH2:43]2)C=1>>[CH3:33][N:31]1[CH:32]=[C:28]([C:24]2[CH:23]=[C:22]([C:19]3[N:20]=[CH:21][C:16]([C:14]4[CH:13]=[N:12][N:11]([CH:42]5[CH2:43][CH2:44][CH:45]([N:48]6[CH2:53][CH2:52][O:51][CH2:50][C:49]6=[O:54])[CH2:46][CH2:47]5)[CH:15]=4)=[CH:17][N:18]=3)[CH:27]=[CH:26][CH:25]=2)[CH:29]=[N:30]1

Participants

3

Reactant 2

HCID 899359682,2,2-Trifluoro-1-[4-(4-{2-[3-(1-methyl-1H-pyrazol-4-yl)-phenyl]-pyrimidin-5-yl}-pyrazol-1-yl)-piperidin-1-yl]-ethanone2×HCID 178516896HCID 178516896, compound2×

Product 1

HCID 729434004-[4-(4-{2-[3-(1-Methyl-1H-pyrazol-4-yl)-phenyl]-pyrimidin-5-yl}-pyrazol-1-yl)-cyclohexyl]-morpholin-3-one

Procedure

The title compound was obtained following procedure described for example 182 but starting from 5-Bromo-2-[3-(1-methyl-1H-pyrazol-4-yl)-phenyl]-pyrimidine (intermediate 2; 230 mg; 0.73 mmol; 1.0 eq.) and trans-4-[4-(4-Iodo-pyrazol-1-yl)-cyclohexyl]-morpholin-3-one (intermediate 26; 274 mg; 0.73 mmol; 1.0 eq.). The crude was purified by recrystallisation in methylisobutylketone. The title compound was obtained as a beige solid (16 mg, 5%). 1H NMR (300 MHz, DMSO) δ 9.16 (s, 2H), 8.54 (s, 2H), 8.40-8.06 (m, 3H), 7.93 (s, 1H), 7.71 (d, J=7.9 Hz, 1H), 7.52 (t, J=7.9 Hz, 1H), 4.31 (d, J=39.6 Hz, 2H), 4.05 (s, 2H), 3.95-3.71 (m, 5H), 2.20 (d, J=11.5 Hz, 2H), 2.03-1.49 (m, 6H), 1.23 (s, 1H), 0.84 (t, J=7.3 Hz, 1H). HPLC (Condition A): Rt 3.31 min (purity 99.2%). MS (ESI+): 484.4.

Workup

  1. customThe crude was purified by recrystallisation in methylisobutylketone

Sources & evidence

ORD record
ord-09c50822fd6b4e0aa3a9e564d09bb2ee
Source dataset
uspto-grants-2015_12
Patent number
US09216991B2

Reaction notes

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