Water → {3-Methyl-4-[3-(3-nitroimidazo[1,2-b]pyridazin-6-ylsulfanyl)propoxy]pyridin-2-yl}-methanol

HRID 1637637Notes

Reaction equation

HRID 1637637 reaction equation
[N+:1]([C:4]1[N:8]2[N:9]=[C:10]([SH:13])[CH:11]=[CH:12][C:7]2=[N:6][CH:5]=1)([O-:3])=[O:2].Cl[CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]([CH2:25][OH:26])[C:20]=1[CH3:27].C(N(CC)CC)C.O>CN(C)C=O>[CH3:27][C:20]1[C:21]([CH2:25][OH:26])=[N:22][CH:23]=[CH:24][C:19]=1[O:18][CH2:17][CH2:16][CH2:15][S:13][C:10]1[CH:11]=[CH:12][C:7]2[N:8]([C:4]([N+:1]([O-:3])=[O:2])=[CH:5][N:6]=2)[N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 18799386[4-(3-Chloropropoxy)-3-methylpyridin-2-yl]methanolHCID 178526776HCID 178526776, compound

Product 1

HCID 18799407{3-Methyl-4-[3-(3-nitroimidazo[1,2-b]pyridazin-6-ylsulfanyl)propoxy]pyridin-2-yl}-methanolYield 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

570 mg (2.9 mmol) of 3-nitroimidazo[1,2-b]pyridazine-6-thiol, 500 mg (2.3 mmol) of [4-(3-chloropropoxy)-3-methylpyridin-2-yl]methanol and 0.4 ml (2.9 mmol) of triethylamine in 10 ml of dimethylformamide are heated to 100° C for 1 h under a nitrogen atmosphere. After cooling to room temperature, water (100 ml) is added and the mixture is extracted with 3×50 ml of ethyl acetate. The residual oil is crystallized from methanol. 600 mg (69%) of the title compound are isolated as a pale beige solid. M.p. 135-136° C.

Workup

  1. extractionthe mixture is extracted with 3×50 ml of ethyl acetate
  2. customThe residual oil is crystallized from methanol

Sources & evidence

ORD record
ord-a634cd2913824daab541310d657f2fc2
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

Loading…