N-methyl-2-pyrrolidone → Methyl 5-[3-fluoro-4-(trifluoromethoxy)phenyl]-1-(thiomorpholin-4-ylcarbonyl)piperidine-3-carboxylate

HRID 661262Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:13]2[CH2:18][N:17]([C:19]([O:21]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:16][CH:15]([C:31]([O:33][CH3:34])=[O:32])[CH2:14]2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].[NH:35]1[CH2:40][CH2:39][S:38][CH2:37][CH2:36]1.C(N(CC)C(C)C)(C)C.CN1CCCC1=O>C(OCC)(=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([CH:13]2[CH2:18][N:17]([C:19]([N:35]3[CH2:40][CH2:39][S:38][CH2:37][CH2:36]3)=[O:21])[CH2:16][CH:15]([C:31]([O:33][CH3:34])=[O:32])[CH2:14]2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:11])([F:12])[F:10]

Participants

Conditions

Temperature: 150 °C

Procedure

2.40 g (4.93 mmol) of the compound from Example 93A, 3.56 g (34.5 mmol) of thiomorpholine and 3.0 ml (2.32 g, 17.3 mmol) of N,N-diisopropylethylamine were added to 28 ml of 1-methyl-2-pyrrolidone and heated in 2 portions in a single-mode microwave (Emrys Optimizer) at 150° C. for 1 h. For workup, the reaction solutions were combined and admixed with water. After addition of ethyl acetate and phase separation, the organic phase was washed with saturated aqueous sodium chloride solution, dried (magnesium sulphate), filtered and concentrated under reduced pressure. Yield: 1.97 g (89% of theory)

Workup

washthe organic phase was washed with saturated aqueous sodium chloride solution
dry with materialdried (magnesium sulphate)
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d083b92ed0c74189b690108017f9d46d
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084469B2

Reaction notes

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