Morpholine → 4-{5-[((2S)-2-Methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinyl)carbonyl]-2-pyridinyl}morpholine hydrochloride

HRID 43422Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][C@@H:11]2[CH3:29])=[O:9])=[CH:4][CH:3]=1.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>C(O)(C)C>[ClH:1].[CH3:29][C@H:11]1[CH2:12][N:13]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:14][CH2:15][N:10]1[C:8]([C:5]1[CH:4]=[CH:3][C:2]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[N:7][CH:6]=1)=[O:9]

Participants

Conditions

Temperature: 120 °C

Procedure

(2S)-1-[(6-Chloro-3-pyridinyl)carbonyl]-2-methyl-4-{[4-(trifluorom ethyl)phenyl]sulfonyl}piperazine (may be prepared as described in Example 26) (67 mg, 0.15 mmol) was weighed into a microwave vial, suspended in isopropanol (1.5 ml) and treated with morpholine (0.261 ml, 2.99 mmol). The mixture was heated in the microwave to 120° C. for 18 h with stirring. LCMS analysis showed clean conversion to product. The reaction mixture was concentrated to give the crude material as a colourless gum. This was purified by MDAP (High pH system) to give the free base of the title compound as a colourless gum (69 mg).

Workup

concentrationThe reaction mixture was concentrated
customto give the crude material as a colourless gum
customThis was purified by MDAP (High pH system)

Sources & evidence

ORD record: ord-493e95539cba4e94bb87759025c3da0a
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536183B2

Reaction notes

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