1,1'-Carbonyldiimidazole → HCID 51357233, compound

HRID 1623747Notes

Reaction equation

HRID 1623747 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.[N:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][N:32]=1>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([NH:37][C:34]1[CH:35]=[CH:36][N:31]=[N:32][CH:33]=1)=[O:9]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 2984924-AminopyridazineHCID 24613572-(Benzyloxy)-5-bromobenzoic acid

Product 1

HCID 51357233HCID 51357233, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Solid 5-bromo-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 5, method C; 200 mg, 0.651 mmol) was added to a stirred suspension of CDI (106 mg, 0.651 mmol) in THF (10 ml) under nitrogen at 20° C. The reaction mixture was stirred at room temperature for 10 min and 4-pyridazinamine (may be prepared as described in Description 11; 61.9 mg, 0.65 mmol) was added dropwise. After refluxing for 14 h, the reaction mixture was concentrated. Water was added to the residue and the mixture was extracted with ethyl acetate (3×50 ml). The organic phase was washed with saturated brine (25 ml), dried over sodium sulphate and evaporated in vacuo. The residue was washed with methanol to yield the title compound as a white solid. 95 mg.

Workup

  1. temperatureAfter refluxing for 14 h
  2. concentrationthe reaction mixture was concentrated
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate (3×50 ml)
  5. washThe organic phase was washed with saturated brine (25 ml)
  6. dry with materialdried over sodium sulphate
  7. customevaporated in vacuo
  8. washThe residue was washed with methanol

Sources & evidence

ORD record
ord-f7cd95f650d040c68eab342ac78e403d
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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