Triethylamine → HCID 90009155, compound

HRID 531288Notes

Reaction equation

HRID 531288 reaction equation
Cl.[F:2][CH:3]1[CH2:6][NH:5][CH2:4]1.[F:7][C:8]([F:57])([F:56])[C:9]1[CH:10]=[C:11]([C@H:19]2[O:23][C:22](=[O:24])[N:21]([CH2:25][C:26]3[C:31]([C:32]4[CH:33]=[C:34]([C:40]5[CH:49]=[CH:48][C:43]([C:44]([O:46][CH3:47])=[O:45])=[CH:42][C:41]=5[CH3:50])[CH:35]=[N:36][C:37]=4[O:38][CH3:39])=[CH:30][N:29]=[C:28](S(C)(=O)=O)[N:27]=3)[C@H:20]2[CH3:55])[CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1.C(N(CC)CC)C>C1COCC1>[F:17][C:15]([F:16])([F:18])[C:13]1[CH:12]=[C:11]([C@H:19]2[O:23][C:22](=[O:24])[N:21]([CH2:25][C:26]3[C:31]([C:32]4[CH:33]=[C:34]([C:40]5[CH:49]=[CH:48][C:43]([C:44]([O:46][CH3:47])=[O:45])=[CH:42][C:41]=5[CH3:50])[CH:35]=[N:36][C:37]=4[O:38][CH3:39])=[CH:30][N:29]=[C:28]([N:5]4[CH2:6][CH:3]([F:2])[CH2:4]4)[N:27]=3)[C@H:20]2[CH3:55])[CH:10]=[C:9]([C:8]([F:7])([F:57])[F:56])[CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 101250543-fluoroazetidine HydrochlorideHCID 90009167HCID 90009167, compound2×

Product 1

HCID 90009155HCID 90009155, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Fluoroazetidine hydrochloride (159 mg, 1.422 mmol), 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, 350 mg, 0.474 mmol), THF (2.4 mL) and triethylamine (330 μl, 2.369 mmol) were stirred at 100° C. for 10 minutes in the microwave reactor. Once complete, the reaction was partitioned between water and ethyl acetate. The organic was then washed with brine, dried over sodium sulfate, filtered and evaporated. The crude was purified by silica gel chromatography, eluting with 25-100% ethyl acetate/hexanes to give the title compound. 1H NMR (CDCl3, 500 MHz): δ 8.21 (d, 1H), 8.17 (s, 1H), 7.98 (s, 1H), 7.92 (d, 1H), 7.88 (s, 1H), 7.73 (s, 2H), 7.47 (d, 1H), 7.31 (d, 1H), 5.68 (d, 1H), 5.51 (m, 0.5H), 5.40 (m, 0.5H), 4.72 (d, 1H), 4.47 (m, 3H), 4.30 (m, 2H), 4.00 (d, s, 4H), 3.93 (s, 3H), 2.37 (s, 3H), 0.74 (d, 3H).

Workup

  1. customOnce complete, the reaction was partitioned between water and ethyl acetate
  2. washThe organic was then washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude was purified by silica gel chromatography
  7. washeluting with 25-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-45d1d2d4099f44ae93b86c857696865f
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

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