Dimethylamine → N,N-Dimethyl-5-[((2S)-2-methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinyl)carbonyl]-2-pyridinamine hydrochloride

HRID 43421Notes

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.[CH3:30][NH:31][CH3:32].CO>C(O)(C)C>[ClH:1].[CH3:30][N:31]([CH3:32])[C:2]1[CH:3]=[CH:4][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:6][N:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

(2S)-1-[(6-Chloro-3-pyridinyl)carbonyl]-2-methyl-4-{[4-(trifluoromethyl)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 (0.75 ml) and treated with dimethylamine, 2M in methanol (0.75 ml, 1.50 mmol). The mixture was heated in the microwave to 120° C. for 18 h with stirring. LCMS analysis showed clean conversion to the product. The reaction mixture was concentrated to give the crude material as a pale yellow gum/solid. This was purified by MDAP (High pH system) to give the free base of the title compound as a colourless gum (61 mg).

Workup

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

Sources & evidence

ORD record: ord-145ff39d9a3d48bdbf15f195d71dfb7f
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536183B2

Reaction notes

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