Morpholine → 3-Methyl-4-[((3s)-3-methyl-4-{[2-methyl-6-(4-morpholinyl)-3-pyridinyl]carbonyl}-1-piperazinyl)sulfonyl]benzonitrile hydrochloride

HRID 43418Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

4-({(3S)-4-[(6-Chloro-2-methyl-3-pyridinyl)carbonyl]-3-methyl-1-piperazinyl}sulfonyl)-3-methylbenzonitrile (may be prepared as described in Example 25) (55 mg, 0.13 mmol) was weighed into a microwave vial, and suspended in isopropanol (1.3 ml). Morpholine (0.221 ml, 2.54 mmol) was added and the mixture was heated in the microwave to 120° C. for 12 h with stirring. LCMS analysis indicated >65% conversion. The reaction mixture was concentrated to give the crude material as a pale yellow gum (78 mg). This was purified by MDAP to give the free base of the title compound as a colourless gum (31 mg).

Workup

concentrationThe reaction mixture was concentrated
customto give the crude material as a pale yellow gum (78 mg)
customThis was purified by MDAP

Sources & evidence

ORD record: ord-edb8feadab7f4b94bbb6a4056333977e
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536183B2

Reaction notes

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