4-(Diphenylmethoxy)-1-piperidinepropaneamine → [6-[3-[4-(Diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[1,5-b]pyridazin-2-yl]carboxylic acid

HRID 1067565Notes

Reaction equation

HRID 1067565 reaction equation
[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:26]1[CH:27]=[CH:28][C:29]2[N:30]([N:32]=[C:33]([C:35]([OH:37])=[O:36])[N:34]=2)[N:31]=1>>[C:19]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:26]3[CH:27]=[CH:28][C:29]4[N:30]([N:32]=[C:33]([C:35]([OH:37])=[O:36])[N:34]=4)[N:31]=3)[CH2:11][CH2:10]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 109693934-(Diphenylmethoxy)-1-piperidinepropaneamineHCID 229892926-Chloro-[1,2,4]triazolo[1,5-b]pyridazine-2-carboxylic acid

Product 1

HCID 22989393[6-[3-[4-(Diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[1,5-b]pyridazin-2-yl]carboxylic acidYield 34.2%

Procedure

2.33 g of 4-(diphenylmethoxy)-1-piperidinepropaneamine and 714 mg of (6-chloro[1,2,4]triazolo[1,5-b]pyridazin-2-yl)carboxylic acid were stirred at 175° C. for 30 minutes. After cooling, the reaction mixture was crystallized by the addition of water-ethyl acetate-ethanol (2:2:1), collected by filtration, washed with water-ethyl acetate-ethyl ether (2:1:2) and dried to yield 598 mg of the title compound.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was crystallized by the addition of water-ethyl acetate-ethanol (2:2:1)
  3. filtrationcollected by filtration
  4. washwashed with water-ethyl acetate-ethyl ether (2:1:2)
  5. customdried

Sources & evidence

ORD record
ord-c9fe0dd6dc1f4c98b6b93455af228c37
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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