Triethylamine → HCID 90009179, compound

HRID 531308Notes

Reaction equation

HRID 531308 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[C:42]([CH3:43])=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][C:34]=5[CH3:44])[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[CH3:49])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Cl.[F:51][CH:52]1[CH2:55][NH:54][CH2:53]1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[F:51][CH:52]1[CH2:55][N:54]([C:21]2[N:20]=[C:19]([CH2:18][N:14]3[C@@H:13]([CH3:49])[C@@H:12]([C:4]4[CH:5]=[C:6]([C:8]([F:10])([F:9])[F:11])[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[C:34]([CH3:44])=[CH:35][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:41][C:42]=4[CH3:43])[CH:28]=[N:29][C:30]=3[O:31][CH3:32])=[CH:23][N:22]=2)[CH2:53]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 101250543-fluoroazetidine HydrochlorideHCID 90009287HCID 90009287, compound2×

Product 1

HCID 90009179HCID 90009179, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 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}-3,5-dimethylbenzoate (INTERMEDIATE 50, 82 mg, 0.117 mmol) in THF (1.5 mL) was added 3-fluoroazetidine hydrochloride (39.2 mg, 0.351 mmol) and triethylamine (0.074 mL, 0.5927 mmol). The resulting mixture was subjected to microwave irradiation at 120° C. for 20 minutes (BIOTAGE microwave). The reaction mixture was diluted with ethyl acetate, washed with water, brine, dried (sodium sulfate), filtered and concentrated to give crude methyl 4-{5-[2-(3-fluoroazetidin-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}-3,5-dimethylbenzoate (82 mg, 0.118 mmol). LCMS (M+H)+: 698.2.

Workup

  1. customirradiation at 120° C. for 20 minutes (BIOTAGE microwave)
  2. washwashed with water, brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b1e9478196b44634a3231007c09b10e2
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

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