3,4-Dimethoxy-1,2,5-thiadiazole 1-oxide → 3-Methoxy-4-[7-(piperidino)hept-5-ynylamino]-1,2,5-thiadiazole-1-oxide

HRID 569556Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:7](OC)=[N:6][S:5](=[O:10])[N:4]=1.[N:11]1([CH2:17][C:18]#[C:19][CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>CO>[CH3:1][O:2][C:3]1[C:7]([NH:24][CH2:23][CH2:22][CH2:21][CH2:20][C:19]#[C:18][CH2:17][N:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)=[N:6][S:5](=[O:10])[N:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3,4-dimethoxy-1,2,5-thiadiazole-1-oxide (2.0 g) in methanol (100 ml) was cooled to 0° C. 7-(Piperidino)hept-5-ynylamine (2.5 g) in methanol (50 ml) was added dropwise with stirring over 30 minutes maintaining the reaction temperature at 0° C. The reaction mixture was stirred at 0° C. for a further 2 hours to give a solution of 3-methoxy-4-[7-(piperidino)hept-5-ynylamino]-1,2,5-thiadiazole-1-oxide. Ammonia gas was bubbled through this solution for 30 minutes and the mixture allowed to stand for 16 hours. The reaction mixture was evaporated under reduced pressure to give an oil which was taken up in ethyl acetate, triturated and cooled to give the title compound (3.0 g), m.p. 134°-6° C. (recrystallisation from isopropanol-ethyl acetate).

Workup

stirringThe reaction mixture was stirred at 0° C. for a further 2 hours

Sources & evidence

ORD record: ord-cf16e0259f764d0f9e04532dbf3bcecc
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04732980

Reaction notes

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