Isopropanol → 3-(5-Nitro-1-methyl-2-imidazolyl)-6-(4-hydroxy-1-piperidinyl-methyleneamino)-s-triazolo[4,3-b]pyridazine

HRID 435595Notes

Reaction equation

HRID 435595 reaction equation
[N+:1]([C:4]1[N:8]([CH3:9])[C:7]([C:10]2[N:14]3[N:15]=[C:16]([N:19]=[CH:20]OCC)[CH:17]=[CH:18][C:13]3=[N:12][N:11]=2)=[N:6][CH:5]=1)([O-:3])=[O:2].C(O)(C)C.O1CCOCC1.[OH:34][CH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>CN1CCCC1=O>[N+:1]([C:4]1[N:8]([CH3:9])[C:7]([C:10]2[N:14]3[N:15]=[C:16]([N:19]=[CH:20][N:38]4[CH2:39][CH2:40][CH:35]([OH:34])[CH2:36][CH2:37]4)[CH:17]=[CH:18][C:13]3=[N:12][N:11]=2)=[N:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 312751,4-DioxaneHCID 79341Piperidin-4-olHCID 214559113-(5-Nitro-1-methyl-2-imidazolyl)-6-ethoxymethyleneamino-s-triazolo[4,3-b]pyridazine

Product 1

HCID 214559433-(5-Nitro-1-methyl-2-imidazolyl)-6-(4-hydroxy-1-piperidinyl-methyleneamino)-s-triazolo[4,3-b]pyridazine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1.2 g. crude 3-(5-nitro-1-methyl-2-imidazolyl)-6-ethoxymethyleneamino-s-triazolo[ 4,3-b]pyridazine dissolved in 13 ml. of a mixture of isopropanol and dioxan ( 7:3), was mixed, N-methylpyrrolidone while stirring at 20° C., with 4-hydroxypiperidine. After 30 minutes, the precipitated crystals were filtered off with suction, washed with isopropanol and water and dried at 120° C. in a vacuum. There was thus obtained 0.6 g. of the desired 3-(5-nitro-1-methyl- 2-imidazolyl)-6-(4-hydroxy-1-piperidinyl-methyleneamino)-s-triazolo[ 4,3-b]-pyridazine, which has a melting point of 188° - 190° C.

Workup

  1. additionwas mixed
  2. filtrationthe precipitated crystals were filtered off with suction
  3. washwashed with isopropanol and water
  4. customdried at 120° C. in a vacuum

Sources & evidence

ORD record
ord-60e03e685d554e678d7bf2e05e3a7bb6
Source dataset
uspto-grants-1977_02
Patent number
US04006141

Reaction notes

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