Trifluoroacetic acid → 3-Chloro-6-(1-piperazinyl)pyridazine

HRID 499143Notes

Reaction equation

HRID 499143 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[N:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:20][C:17]1[N:16]=[N:15][C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21925370tert-Butyl 4-(6-chloropyridazin-3-yl)piperazine-1-carboxylate

Product 1

HCID 52949263-Chloro-6-(1-piperazinyl)pyridazineYield 75.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of 4-(6-chloropyridazin-3-yl)piperazine-1-carboxylic acid tert-butyl ester (2.00 g, 6.69 mmol) in dichloromethane (10 mL) was carefully added trifluoroacetic acid (2 mL). The mixture was stirred for 45 minutes at room temperature and then concentrated in vacuo to afford the crude 3-chloro-6-piperazin-1-ylpyridazine (˜1.0 g) which was used in the next reaction without further purification. MS (ES+) m/z 199.1 (M+1).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4941d465b620445481618ce9b465f7d7
Source dataset
uspto-grants-2010_08
Patent number
US07767677B2

Reaction notes

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