Sodium Hydroxide → N-[6-[3-[4-(diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[1,5-b]pyridazine-2-carbonyl]glycine

HRID 1169106Notes

Reaction equation

HRID 1169106 reaction equation
C([O:3][C:4](=[O:42])[CH2:5][NH:6][C:7]([C:9]1[N:17]=[C:16]2[N:11]([N:12]=[C:13]([NH:18][CH2:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([O:28][CH:29]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:24][CH2:23]3)[CH:14]=[CH:15]2)[N:10]=1)=[O:8])C.[OH-].[Na+]>C(O)C>[C:36]1([CH:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:28][CH:25]2[CH2:24][CH2:23][N:22]([CH2:21][CH2:20][CH2:19][NH:18][C:13]3[CH:14]=[CH:15][C:16]4[N:11]([N:10]=[C:9]([C:7]([NH:6][CH2:5][C:4]([OH:42])=[O:3])=[O:8])[N:17]=4)[N:12]=3)[CH2:27][CH2:26]2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22989377N-[6-[3-[4-(diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[1,5-b]pyridazine-2-carbonyl]glycine ethyl ester

Product 1

HCID 22989431N-[6-[3-[4-(diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[1,5-b]pyridazine-2-carbonyl]glycineYield 50.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

928 mg of N-[6-[3-[4-(diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[1,5-b]pyridazine-2-carbonyl]glycine ethyl ester was dissolved in 7 ml of ethanol; 2.2 ml of a 1 N aqueous solution of sodium hydroxide was added, followed by stirring at room temperature for 1.5 hours. The mixture was concentrated under reduced pressure. The residue was diluted with water; 1 N hydrochloric acid was added to bring the mixture to pH 4.5. The crystal obtained was collected by filtration, washed with water, acetone and ethyl acetate and dried to yield 443 mg of the title compound.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. addition1 N hydrochloric acid was added
  4. customThe crystal obtained
  5. filtrationwas collected by filtration
  6. washwashed with water, acetone and ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-3a39bd3fe2ce4137a7687896c58c368f
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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