Triethylamine → HCID 90009210, compound

HRID 531306Notes

Reaction equation

HRID 531306 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:12]2[O:16][C:15](=[O:17])[N:14]([CH2:18][C:19]3[C:24]([C:25]4[CH:26]=[C:27]([C:33]5[CH:45]=[CH:44][C:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[CH:35][C:34]=5[CH3:46])[CH:28]=[N:29][C:30]=4[O:31][CH3:32])=[CH:23][N:22]=[C:21](S(C)(=O)=O)[N:20]=3)[C@H:13]2[CH3:51])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Cl.[F:53][C:54]1([F:58])[CH2:57][NH:56][CH2:55]1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[F:53][C:54]1([F:58])[CH2:57][N:56]([C:21]2[N:20]=[C:19]([CH2:18][N:14]3[C@@H:13]([CH3:51])[C@@H:12]([C:4]4[CH:5]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:7]=[C:2]([F:1])[CH:3]=4)[O:16][C:15]3=[O:17])[C:24]([C:25]3[CH:26]=[C:27]([C:33]4[CH:45]=[CH:44][C:36]([C:37]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38])=[CH:35][C:34]=4[CH3:46])[CH:28]=[N:29][C:30]=3[O:31][CH3:32])=[CH:23][N:22]=2)[CH2:55]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 90009289HCID 90009289, compound2×

Product 1

HCID 90009210HCID 90009210, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-{5-[4-({(4S,5R)-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-2-(methylsulfonyl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3-methylbenzoate (INTERMEDIATE 48, 96 mg, 0.131 mmol) in THF (1.5 mL) was added 3,3-difluoroazetidine hydrochloride (51.1 mg, 0.394 mmol) and triethylamine (0.082 mL, 0.591 mmol). The resulting mixture was subjected to microwave irradiation at 135° C. for 40 minutes. The reaction mixture was diluted with ethyl acetate, washed with water, brine, dried (sodium sulfate), filtered and concentrated to give crude tert-butyl 4-{5-[2-(3,3-difluoroazetidin-1-yl)-4-({(4S,5R)-5-[3-fluoro-5-(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)pyrimidin-5-yl]-6-methoxypyridin-3-yl}-3-methylbenzoate (98 mg, 0.131 mmol). LCMS (M+H)+: 744.2.

Workup

  1. customirradiation at 135° C. for 40 minutes
  2. washwashed with water, brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a67d8bbdbd634a9589cd162e033d2f64
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

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