Thiomorpholine → Methyl 5-[3-fluoro-4-(2,2,2-trifluoroethyl)phenyl]-1-(thiomorpholin-4-ylcarbonyl)piperidine-3-carboxylate

HRID 661250Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:13]2[CH2:18][N:17]([C:19](OC3C=CC([N+]([O-])=O)=CC=3)=[O:20])[CH2:16][CH:15]([C:31]([O:33][CH3:34])=[O:32])[CH2:14]2)[CH:5]=[CH:6][C:7]=1[CH2:8][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>[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:20])[CH2:16][CH:15]([C:31]([O:33][CH3:34])=[O:32])[CH2:14]2)[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]([F:10])([F:12])[F:11]

Participants

Conditions

Temperature: 150 °C

Procedure

A solution of 5.85 g (9.54 mmol, purity 80%) of the compound from Example 77A in 1-methyl-2-pyrrolidone (50 ml) was admixed with 5.43 ml (5.91 g, 57.2 mmol) of thiomorpholine and 4.99 ml (3.70 g, 28.6 mmol) of N,N-diisopropylethylamine and then heated in 4 portions in a single-mode microwave (Emrys Optimizer) at 150° C. for 45 min. For workup, the reaction solutions were combined and purified directly by means of preparative HPLC. Yield: 4.29 g (93% of theory)

Workup

custompurified directly by means of preparative HPLC

Sources & evidence

ORD record: ord-44428c82885f4281b47354b8c401b741
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084469B2

Reaction notes

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