1,8-Diazabicyclo(5.4.0)undec-7-ene → [2-(1H-Benzimidazol-2-ylsulfanylmethyl)-3-chloro-pyridin-4-yl]methyl-[2-(3-nitroimidazo[1,2-b]pyridazin-6-ylsulfanyl)ethyl]amine

HRID 1637639Notes

Reaction equation

HRID 1637639 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][CH2:11][C:12]1[C:17]([Cl:18])=[C:16](N(CCCl)C)[CH:15]=[CH:14][N:13]=1.[N+:24]([C:27]1[N:31]2[N:32]=[C:33]([SH:36])[CH:34]=[CH:35][C:30]2=[N:29][CH:28]=1)([O-:26])=[O:25].C1CCN2[C:40](=[N:41][CH2:42]CC2)[CH2:39]C1>CN(C)C=O>[NH:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[S:10][CH2:11][C:12]1[C:17]([Cl:18])=[C:16]([CH2:42][NH:41][CH2:40][CH2:39][S:36][C:33]2[CH:34]=[CH:35][C:30]3[N:31]([C:27]([N+:24]([O-:26])=[O:25])=[CH:28][N:29]=3)[N:32]=2)[CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53762852[2-(1H-benzimidazol-2-ylsulfanylmethyl)-3-chloropyridin-4-yl]-(2-chloroethyl)methyl-amineHCID 178526776HCID 178526776, compound

Product 1

HCID 70272959[2-(1H-Benzimidazol-2-ylsulfanylmethyl)-3-chloro-pyridin-4-yl]methyl-[2-(3-nitroimidazo[1,2-b]pyridazin-6-ylsulfanyl)ethyl]amineYield 66.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.44 g (1.0 mmol) of [2-(1H-benzimidazol-2-ylsulfanylmethyl)-3-chloropyridin-4-yl]-(2-chloroethyl)methyl-amine, 0.24 g (1.2 mmol) of 3-nitroimidazo[1,2-b]pyridazine-6-thiol and 0.52 ml (3.5 mmol) of DBU are reacted in 10 ml of dimethylformamide by the procedure described in Example 16. After crystallization from diisopropyl ether, 0.35 g (66%) of the title compound is obtained as a pale beige solid. M.p. 184-185° C.

Workup

  1. customAfter crystallization from diisopropyl ether

Sources & evidence

ORD record
ord-f94b071998c5424a8558987538b87889
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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