Thiomorpholine → {3-[4-(2,2-Difluoroethyl)phenyl]-5-[3-(2-methoxyethyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}(thiomorpholin-4-yl)methanone

HRID 220052Notes

Reaction equation

HRID 220052 reaction equation
[F:1][CH:2]([F:37])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH:14]([C:16]3[O:20][N:19]=[C:18]([CH2:21][CH2:22][O:23][CH3:24])[N:17]=3)[CH2:13][N:12]([C:25](OC3C=CC([N+]([O-])=O)=CC=3)=[O:26])[CH2:11]2)=[CH:6][CH:5]=1.[NH:38]1[CH2:43][CH2:42][S:41][CH2:40][CH2:39]1.C(N(CC)C(C)C)(C)C>CN1CCCC1=O>[F:1][CH:2]([F:37])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH:14]([C:16]3[O:20][N:19]=[C:18]([CH2:21][CH2:22][O:23][CH3:24])[N:17]=3)[CH2:13][N:12]([C:25]([N:38]3[CH2:43][CH2:42][S:41][CH2:40][CH2:39]3)=[O:26])[CH2:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 67164ThiomorpholineHCID 81531DiisopropylethylamineHCID 596065764-Nitrophenyl 3-[4-(2,2-difluoroethyl)phenyl]-5-[3-(2-methoxyethyl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxylate

Product 1

HCID 59606564{3-[4-(2,2-Difluoroethyl)phenyl]-5-[3-(2-methoxyethyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}(thiomorpholin-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 56.0 mg (0.065 mmol, purity 60%) of the compound from Example 62A in 1-methyl-2-pyrrolidone (2.0 ml) was admixed with 37.0 μl (40.0 mg, 0.390 mmol) of thiomorpholine and 34.0 μl (25.0 mg, 0.195 mmol) of N,N-diisopropylethylamine and then heated in a single-mode microwave (Emrys Optimizer) at 150° C. for 30 min. For workup, the reaction solutions were combined and purified directly by means of preparative HPLC. Yield: 14.7 mg (47% of theory)

Workup

  1. custompurified directly by means of preparative HPLC

Sources & evidence

ORD record
ord-a89d5348868a4001b44b94d681aac90d
Source dataset
uspto-grants-2012_06
Patent number
US08202862B2

Reaction notes

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