Nitrogen → HCID 59484963, compound

HRID 925494Notes

Reaction equation

HRID 925494 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2C(=O)NN=[CH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].N#N.[Cl-].[Cl-].[Ca+2].[CH3:21][N:22]([CH3:42])[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:28]=[N:29][C:30]([C:33]2[CH:34]=[C:35]([CH:39](O)[CH3:40])[CH:36]=[CH:37][CH:38]=2)=[N:31][CH:32]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:62]([C:71](OC(C)(C)C)=[O:72])=[N:63]C(OC(C)(C)C)=O>CO.CN(C=O)C.C1COCC1>[CH3:21][N:22]([CH3:42])[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:28]=[N:29][C:30]([C:33]2[CH:34]=[C:35]([CH:39]([N:62]3[C:71](=[O:72])[CH:13]=[CH:14][C:9]([C:5]4[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=4)[C:1]#[N:2])=[N:63]3)[CH3:40])[CH:36]=[CH:37][CH:38]=2)=[N:31][CH:32]=1

Participants

10

Reactant 6

HCID 947NitrogenHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 5284359Calcium ChlorideHCID 59484885HCID 59484885, compoundHCID 67439965HCID 67439965, compound

Product 1

HCID 59484963HCID 59484963, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

197 mg of 3-cyanophenylpyridazinone (1.00 mmol) is suspended in a mixture of 5 ml of abs. THF and 1 ml of abs. DMF in an N2-flushed apparatus with CaCl2 protection, 301 mg of 1-{3-[5-(3-dimethylaminopropoxy)-pyrimidin-2-yl]phenyl}ethanol (1.00 mmol) and 500 mg of polymer-bound triphenylphosphine (1.5 mmol) are added, the mixture is stirred at RT for 30 min, 345 mg of di-tert-butyl azodicarboxylate (1.5 mmol) are subsequently added with ice/H2O cooling and stirring, and the mixture is stirred at RT for a further 2 h. For work-up, the reaction mixture is diluted with 10 ml of methanol, and the polymer is removed by filtration. The residue is washed with dichloromethane, and the combined filtrate is evaporated to dryness in a rotary evaporator and purified by chromatography (silica gel: DCM+0-30% of MeOHF), giving “A298”, m.p. 105-7° C.

Workup

  1. additionare added
  2. stirringstirring
  3. stirringthe mixture is stirred at RT for a further 2 h
  4. customthe polymer is removed by filtration
  5. washThe residue is washed with dichloromethane
  6. customthe combined filtrate is evaporated to dryness in a rotary evaporator
  7. custompurified by chromatography (silica gel: DCM+0-30% of MeOHF)
  8. customgiving “A298”, m.p. 105-7° C.

Sources & evidence

ORD record
ord-dc76e7ff6a9d48ebba6d7e4d88de63d6
Source dataset
uspto-grants-2016_03
Patent number
US09284300B2

Reaction notes

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