Imidazole → HCID 118021435, compound

HRID 531300Notes

Reaction equation

HRID 531300 reaction equation
[F:1][C:2]([F:51])([F:50])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:27]=[C:28]([C:34]5[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][C:35]=5[CH3:44])[CH:29]=[N:30][C:31]=4[O:32][CH3:33])=[CH:24][N:23]=[C:22](S(C)(=O)=O)[N:21]=3)[C@H:14]2[CH3:49])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[NH:52]1[CH:56]=[CH:55][N:54]=[CH:53]1>O1CCOCC1>[F:1][C:2]([F:51])([F:50])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:27]=[C:28]([C:34]5[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][C:35]=5[CH3:44])[CH:29]=[N:30][C:31]=4[O:32][CH3:33])=[CH:24][N:23]=[C:22]([N:52]4[CH:56]=[CH:55][N:54]=[CH:53]4)[N:21]=3)[C@H:14]2[CH3:49])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 90009167HCID 90009167, compound2×

Product 1

HCID 118021435HCID 118021435, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 4-{5-[4-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(methylsulfonyl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3-methylbenzoate (INTERMEDIATE 46, 125 mg, 0.169 mmol), 1,4-dioxane (1.1 mL) and imidazole (57.6 mg, 0.846 mmol) were stirred at 80° C. for 20 minutes in a 1 dram vial. LCMS shows about 2/3 conversion to target. Dropped temperature to 40° C., and stirred overnight, at which time LCMS showed reaction is complete. The reaction was directly purified by silica gel chromatography, eluting with 20-100% ethyl acetate/hexanes to give the titled compound. 1H NMR (CDCl3, 500 MHz): δ 8.64 (s, 1H), 8.56 (s, 1H), 8.30 (d, 1H), 8.00 (s, 1H), 7.94 (d, 1H), 7.90 (s, 2H), 7.75 (s, 2H), 7.57 (d, 1H), 7.33 (d, 1H), 7.22 (s, 1H), 5.75 (d, 1H), 4.91 (d, 1H), 4.46 (m, 1H), 4.20 (d, 1H), 4.03 (s, 3H), 3.94 (s, 3H), 2.39 (s, 3H), 0.81 (d, 3H).

Workup

  1. additionDropped temperature to 40° C.
  2. customreaction
  3. customThe reaction was directly purified by silica gel chromatography
  4. washeluting with 20-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-dc67ed85cc4649928142f9b4866235af
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

Loading…