Azetidine → 6-(5-Azetidin-1-yl-pent-1-ynyl)-3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazole

HRID 270348Notes

Reaction equation

HRID 270348 reaction equation
[F:1][C:2]([F:29])([F:28])[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][CH2:21][CH2:22]OS(C)(=O)=O)=[CH:17][C:12]=3[S:11][N:10]=2)=[CH:5][CH:4]=1.[NH:30]1[CH2:33][CH2:32][CH2:31]1>>[N:30]1([CH2:22][CH2:21][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:29])([F:28])[F:1])=[CH:4][CH:5]=4)=[N:10][S:11][C:12]=3[CH:17]=2)[CH2:33][CH2:32][CH2:31]1

Participants

3

Reactant 2

HCID 10422AzetidineHCID 86585421Methanesulfonic acid 5-[3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazol-6-yl]-pent-4-ynyl ester

Product 1

HCID 101578096-(5-Azetidin-1-yl-pent-1-ynyl)-3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazole

Procedure

In analogy to example 17.1, Methanesulfonic acid 5-[3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazol-6-yl]-pent-4-ynyl ester and azetidine were converted to yield 6-(5-Azetidin-1-yl-pent-1-ynyl)-3-(4-trifluoromethyl-phenyl)-benzo[d]isothiazole as orange oil, MS: 401 (MH+).

Sources & evidence

ORD record
ord-309a7551f45348bc9ced0e630cd344b9
Source dataset
uspto-grants-2008_11
Patent number
US07449483B2

Reaction notes

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