Water → HCID 57442331, compound

HRID 2262711Notes

Reaction equation

HRID 2262711 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([N:17]3[CH2:22][CH2:21][N:20]([CH:23]4[CH2:26][CH2:25][CH2:24]4)[CH2:19][CH2:18]3)=[O:16])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.O.[CH3:28][N:29](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH:23]1([N:20]2[CH2:21][CH2:22][N:17]([C:15](=[O:16])[CH2:14][N:11]3[CH2:12][CH2:13][N:8]([C:5]4[N:4]=[N:3][C:2]([C:28]#[N:29])=[CH:7][CH:6]=4)[CH2:9][CH2:10]3)[CH2:18][CH2:19]2)[CH2:26][CH2:25][CH2:24]1

Participants

7

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 57443120HCID 57443120, compound

Product 1

HCID 57442331HCID 57442331, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

In a sealed tube, dissolve 3-chloro-6-{4-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]piperazin-1-yl}pyridazine (205 mg, 0.541 mmol), Zn(CN)2 (39 mg, 0.325 mmol), Pd2dba3 (12.3 mg, 0.0135 mmol) and DPPF (15 mg, 0.027 mmol) in DMF (3 mL). Add I drop of H2O and degas the solution with N2. Seal the tube and heat at 120° C. overnight. Cool and dilute with 3 N HCl (30 mL). Extract with CH2Cl2 (2×25 mL). Discard these extracts. Basify the aqueous layer with 10 N NaOH and extract with CH2Cl2 (3×35 mL). Combine, dry (MgSO4) and evaporate the organic extracts to yield the title compound. 1H NMR (CDCl3) δ 7.44 (d, 1H), 6.83 (d, 1H), 3.84-3.1 (m, 4H), 3.66-3.58 (m, 4H), 3.26 (s, 2H), 2.75-2.66 (m, 5H), 2.33-2.29 (m, 4H), 2.07-2.01 (m, 2H), 1.91-1.85 (m, 2H), 1.76-1.70 (m, 2H); LC-MS (M+1) 370.00.

Workup

  1. additionAdd I
  2. customdegas the solution with N2
  3. customSeal the tube
  4. temperatureCool
  5. additiondilute with 3 N HCl (30 mL)
  6. extractionExtract with CH2Cl2 (2×25 mL)
  7. extractionBasify the aqueous layer with 10 N NaOH and extract with CH2Cl2 (3×35 mL)
  8. dry with materialCombine, dry (MgSO4)
  9. customevaporate the organic extracts

Sources & evidence

ORD record
ord-25ee9cdb44a04581b619a16f8ad6623a
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

Loading…