Azetidine → HCID 67028737, compound

HRID 43424Notes

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[CH2:33][CH2:32][CH2:31]1>C(O)(C)C>[ClH:1].[N:30]1([C:2]2[N:7]=[CH:6][C:5]([C:8]([N:10]3[CH2:15][CH2:14][N:13]([S:16]([C:19]4[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=4)(=[O:18])=[O:17])[CH2:12][C@@H:11]3[CH3:29])=[O:9])=[CH:4][CH:3]=2)[CH2:33][CH2:32][CH2:31]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) (69 mg, 0.154 mmol) was transferred into a microwave vial as a solution in isopropanol (1.5 ml). Azetidine (0.208 ml, 3.08 mmol) was added and the clear solution was heated in the microwave to 120° C. for 12 h with stirring. LCMS analysis showed complete conversion. The reaction mixture was concentrated to give the crude material as a colourless gum (206 mg). This was purified by MDAP (High pH system) to give the free base of the title compound as a colourless gum (65 mg).

Workup

concentrationThe reaction mixture was concentrated
customto give the crude material as a colourless gum (206 mg)
customThis was purified by MDAP (High pH system)

Sources & evidence

ORD record: ord-61a91b39c8064fff9ca52bbee2c5bc7c
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536183B2

Reaction notes

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