Dimethylamine → N,N,6-Trimethyl-5-[((2S)-2-methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinyl)carbonyl]-2-pyridinamine hydrochloride

HRID 43416Notes

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

Participants

Conditions

Temperature: 120 °C

Procedure

(2S)-1-[(6-Chloro-2-methyl-3-pyridinyl)carbonyl]-2-methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (may be prepared as described in Example 24) (65 mg, 0.14 mmol) was weighed into a microwave vial, and suspended in isopropanol (0.7 ml). Dimethylamine, 2M in methanol (0.7 ml, 1.40 mmol) was added, and the mixture was stirred briefly to give a clear solution. This was heated in the microwave to 120° C. for 4 h with stirring. The reaction mixture was concentrated to give the crude material as a yellow gum, which was purified by MDAP to give the free base of the title compound as a colourless gum (47 mg).

Workup

customto give a clear solution
stirringwith stirring
concentrationThe reaction mixture was concentrated
customto give the crude material as a yellow gum, which
customwas purified by MDAP

Sources & evidence

ORD record: ord-1d925e0f10454b9cbb0756ab10bf0d56
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536183B2

Reaction notes

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