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

HRID 1505716Notes

Reaction equation

HRID 1505716 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[CH2:52][CH2:51][O:50][C:49]3=[O:53])[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[CH2:52][CH2:51][O:50][C:49]6=[O:53])[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 178519155HCID 178519155, compound2×

Product 1

HCID 899357643-[4-(4-{2-[3-(1-Methyl-1H-pyrazol-4-yl)-phenyl]-pyrimidin-5-yl}-pyrazol-1-yl)-cyclohexyl]-oxazolidin-2-oneYield 51%

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; 200 mg; 0.63 mmol; 1.0 eq.) and trans-3-[4-(4-Iodo-pyrazol-1-yl)-cyclohexyl]-oxazolidin-2-one (intermediate 27; 231 mg; 0.63 mmol; 1.0 eq.). The crude was triturated in acetonitrile and the suspension filtered and dried under vacuum to afford the title compound as a brown solid (151 mg, 51%). 1H NMR (300 MHz, DMSO) δ 9.21 (s, 2H), 8.58 (d, J=3.6 Hz, 2H), 8.38-8.10 (m, 3H), 7.98 (s, 1H), 7.86-7.44 (m, 2H), 4.32 (dd, J=14.8, 6.5 Hz, 3H), 3.95 (s, 3H), 3.78-3.46 (m, 4H), 2.23 (s, 2H), 2.08-1.57 (m, 7H). HPLC (Condition A): Rt 3.39 min (purity 97.9%). MS (ESI+): 470.4.

Workup

  1. customThe crude was triturated in acetonitrile
  2. filtrationthe suspension filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-b0ed8f83368149ed934ee33ae62efa99
Source dataset
uspto-grants-2015_12
Patent number
US09216991B2

Reaction notes

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