Trifluoroacetic acid → HCID 58579905, compound

HRID 2059855Notes

Reaction equation

HRID 2059855 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]2[CH:11]=[N:12][N:13](C(OC(C)(C)C)=O)[C:14](=[O:16])[CH:15]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]2[CH:11]=[N:12][NH:13][C:14](=[O:16])[CH:15]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58579932HCID 58579932, compound

Product 1

HCID 58579905HCID 58579905, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-((4-chlorophenylthio)methyl)-6-oxopyridazine-1(6H)-carboxylate Part C (137 mg, 0.34 mmol) in CH2Cl2 (5 mL) was added TFA (1.50 mL, 19.41 mmol). The mixture was stirred at RT for 15 min before being concentrated. The crude product was subjected to flash chromatography (silica gel/hexane-EtOAc 100:0 to 0:100 gradient, using LC-MS to identify fractions containing the desired product) to afford 5-((4-chlorophenylthio)methyl)pyridazin-3(2H)-one 7D (81 mg, 81% yield). 1H NMR (400 MHz, Chloroform-D) δ ppm 7.76 (1H, d, J=2.01 Hz), 7.27 (4H, s), 6.56 (1H, s), 3.82 (2H, s).

Workup

  1. concentrationbefore being concentrated
  2. additioncontaining the desired product)

Sources & evidence

ORD record
ord-206971d4b8b9468b8f346ffcecc24205
Source dataset
uspto-grants-2012_10
Patent number
US08278316B2

Reaction notes

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