Toluene → 2-(4-Chlorophenyl)-6-{[6-(piperidin-4-yloxy)pyridin-2-yl]methyl}thieno[2,3-d]pyridazin-7(6H)-one

HRID 2239364Notes

Reaction equation

HRID 2239364 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:38][C:11]3[C:12](=[O:37])[N:13]([CH2:16][C:17]4[N:22]=[C:21]([O:23][CH:24]5[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]5)[CH:20]=[CH:19][CH:18]=4)[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.C1(C)C=CC=CC=1>C(Cl)Cl.C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:38][C:11]3[C:12](=[O:37])[N:13]([CH2:16][C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([O:23][CH:24]5[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]5)[N:22]=4)[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 1140TolueneHCID 68711796tert-Butyl 4-[(6-{[2-(4-chlorophenyl)-7-oxothieno[2,3-d]pyridazin-6(7H)-yl]methyl}pyridin-2-yl)oxy]piperidine-1-carboxylate

Product 1

HCID 687073382-(4-Chlorophenyl)-6-{[6-(piperidin-4-yloxy)pyridin-2-yl]methyl}thieno[2,3-d]pyridazin-7(6H)-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-butyl 4-[(6-{[2-(4-chlorophenyl)-7-oxothieno[2,3-d]pyridazin-6(7H)-yl]methyl}pyridin-2-yl)oxy]piperidine-1-carboxylate (0.22 g, 0.39 mmol) was dissolved in DCM/TFA 5:1 (6 mL) and stirred for 1 hour. The reaction mixture was co-evaporated with toluene, dissolved in DCM (20 mL) and washed with sat. NaHCO3(aq.)/water 1:1 (30 mL). The resulting water phase was extracted with DCM (3×20 mL). The combined organics were dried over a phase separator and concentrated in vacuo to give the product. Yield: 0.16 g (89%). MS (ESI+) 453.06 (M+1H+).

Workup

  1. washwashed with sat. NaHCO3(aq.)/water 1:1 (30 mL)
  2. extractionThe resulting water phase was extracted with DCM (3×20 mL)
  3. customThe combined organics were dried over a phase separator
  4. concentrationconcentrated in vacuo
  5. customto give the product

Sources & evidence

ORD record
ord-79d1a024d0e947948477b373829a7618
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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