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Dimethylformamide → HCID 68283666, compound

HRID 1527313
Notes
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Reaction equation

HRID 1527313 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][N:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][C:12]([O:14]C)=[O:13])[N:3]=1.C(Cl)Cl.C[N:20]([CH:22]=[O:23])C>O.[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.Cl[Pd]Cl.[Fe+2]>[C:22]([C:2]1[C:10]2[C:5](=[N:6][N:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][C:12]([OH:14])=[O:13])[N:3]=1)(=[O:23])[NH2:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 68283346HCID 68283346, compound

Product 1

HCID 68283666HCID 68283666, compound

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst
HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst
HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 2-(3-iodo-1H-pyrazolo[3,4-c]pyridazin-1-yl)acetate (675 mg, 2.12 mmol) in DMF (7.5 mL) and water (1.5 mL) was added Zn(CN)2 (274 mg, 2.33 mmol), Pd2 dba3 (194 mg, 0.21 mmol) and PdCl2(dppf).CH2Cl2 adduct (173 mg, 0.21 mmol). The reaction mixture was stirred at 100° C. for 16 h. The resulting suspension was filtered and the filtrate was evaporated under vacuum. The residue was suspended in CH3CN/MeOH 1:1, the solid was filtered off and the filtrate was purified by preparative HPLC (Macherey Nagel, VP250/40, C18 Nucleosil 100-10, flow: 40 mL/min, eluent: 5-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA) to give the title compound after lyophilisation. MS (LC/MS): 222.1 [M+H]+; tR (HPLC conditions c): 1.34 min.

Workup

  1. filtrationThe resulting suspension was filtered
  2. customthe filtrate was evaporated under vacuum
  3. filtrationthe solid was filtered off
  4. customthe filtrate was purified by preparative HPLC (Macherey Nagel, VP250/40, C18 Nucleosil 100-10, flow: 40 mL/min, eluent: 5-100% CH3CN/H2O/20 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA)

Sources & evidence

ORD record
ord-cf1f7ed7f1454ae6aa95e116dd12de49
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09085555B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes