Azetidine → (2s)-1-{[6-(1-Azetidinyl)-2-methyl-3-pyridinyl]carbonyl}-2-methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine hydrochloride

HRID 43420Notes

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.[NH:31]1[CH2:34][CH2:33][CH2:32]1>C(O)(C)C>[ClH:1].[N:31]1([C:2]2[N:7]=[C:6]([CH3:8])[C:5]([C:9]([N:11]3[CH2:16][CH2:15][N:14]([S:17]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)(=[O:19])=[O:18])[CH2:13][C@@H:12]3[CH3:30])=[O:10])=[CH:4][CH:3]=2)[CH2:34][CH2:33][CH2:32]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) (66 mg, 0.14 mmol) was transferred into a microwave vial as a solution in isopropanol (1.4 ml). Azetidine (0.163 ml, 2.42 mmol) was added and the clear solution was heated in the microwave to 120° C. for 18 h with stirring. LCMS analysis showed >80% conversion. The reaction mixture was concentrated to give the crude material as a colourless gum (˜200 mg). This was purified by MDAP to give the free base of the title compound as a brown gum (45 mg).

Workup

concentrationThe reaction mixture was concentrated
customto give the crude material as a colourless gum (˜200 mg)
customThis was purified by MDAP

Sources & evidence

ORD record: ord-9fa2a248b7d240ba96f81f320a9f5000
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536183B2

Reaction notes

Loading…