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

HRID 977984Notes

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 temprature 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-572cb061cf4f41a0b681814322d23934
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04663331

Reaction notes

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