Azetidine → 6-(3-Azetidin-1-yl-prop-1-ynyl)-3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazole

HRID 270351Notes

Reaction equation

HRID 270351 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3[CH:14]=[CH:15][C:16]([C:18]#[C:19][CH2:20]OS(C)(=O)=O)=[CH:17][C:12]=3[S:11][N:10]=2)=[CH:5][CH:4]=1.[NH:28]1[CH2:31][CH2:30][CH2:29]1>>[N:28]1([CH2:20][C:19]#[C:18][C:16]2[CH:15]=[CH:14][C:13]3[C:9]([C:6]4[CH:7]=[CH:8][C:3]([C:2]([F:27])([F:26])[F:1])=[CH:4][CH:5]=4)=[N:10][S:11][C:12]=3[CH:17]=2)[CH2:31][CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 10422AzetidineHCID 86585422Methanesulfonic acid 3-[3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazol-6-yl]-prop-2-ynyl ester

Product 1

HCID 99694946-(3-Azetidin-1-yl-prop-1-ynyl)-3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazole

Procedure

In analogy to example 17.1, Methanesulfonic acid 3-[3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazol-6-yl]-prop-2-ynyl ester and azetidine were converted to yield 6-(3-Azetidin-1-yl-prop-1-ynyl)-3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazole as light brown oil, MS: 373 (MH+).

Sources & evidence

ORD record
ord-171f69398b1b41a28c31a7d5db4cb336
Source dataset
uspto-grants-2008_11
Patent number
US07449483B2

Reaction notes

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