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1-Butanol → tert-Butyl 4-(6-(2-methoxy-4-(1H-pyrazol-1-yl)phenyl)pyridazin-3-yl)piperazine-1-carboxylate

HRID 1027194
Notes
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Reaction equation

HRID 1027194 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH:18]=[CH:17][CH:16]=[N:15]3)=[CH:10][C:9]=2[O:19][CH3:20])=[CH:6][CH:7]=1.[N:21]1([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.CCN(C(C)C)C(C)C.C(O)CCC>CCOC(C)=O>[CH3:20][O:19][C:9]1[CH:10]=[C:11]([N:14]2[CH:18]=[CH:17][CH:16]=[N:15]2)[CH:12]=[CH:13][C:8]=1[C:5]1[N:4]=[N:3][C:2]([N:24]2[CH2:23][CH2:22][N:21]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25]2)=[CH:7][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 2631-ButanolHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 867105443-Chloro-6-[2-methoxy-4-(1H-pyrazol-1-yl)phenyl]pyridazine

Product 1

HCID 86710592tert-Butyl 4-(6-(2-methoxy-4-(1H-pyrazol-1-yl)phenyl)pyridazin-3-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Following GENERAL METHOD 6-1 for SNAr, Intermediate 2-1 (50 mg, 0.174 mmol), tert-butyl piperazine-1-carboxylate (59 mg, 0.314 mmol), DIPEA (0.06 mL, 0.349 mmol), and n-butanol (0.1 mL) were combined in a 4 mL reaction vial and heated at 120° C. overnight. The reaction was cooled to RT and EtOAc was added. The white solid that formed was filtered off and washed with EtOAc, dissolved in DCM and washed with H2O. The organic layer was dried with sodium sulfate, filtered, and concentrated in vacuo to afford the desired product.

Workup

  1. customwere combined in a 4 mL reaction vial
  2. temperatureThe reaction was cooled to RT
  3. customThe white solid that formed
  4. filtrationwas filtered off
  5. washwashed with EtOAc
  6. dissolutiondissolved in DCM
  7. washwashed with H2O
  8. dry with materialThe organic layer was dried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-da1a772a078e447ba5d0fe9a27d41c20
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08729263B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes