1,2-Dichloroethane → HCID 86668214, compound

HRID 1623824Notes

Reaction equation

HRID 1623824 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][N:2]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N1CCOCC1)C.[F:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][O:38][C:39]2[CH:47]=[CH:46][C:45]([CH:48]=[O:49])=[CH:44][C:40]=2[C:41](O)=[O:42])=[CH:33][CH:32]=1>CN(C)C=O>[F:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][O:38][C:39]2[CH:47]=[CH:46][C:45]([CH:48]=[O:49])=[CH:44][C:40]=2[C:41]([NH:7][C:4]2[CH:5]=[CH:6][N:1]=[N:2][CH:3]=2)=[O:42])=[CH:33][CH:32]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 2984924-AminopyridazineHCID 86668206HCID 86668206, compound

Product 1

HCID 86668214HCID 86668214, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Pyridazinamine (0.52 g, 5.47 mmol), EDC (0.84 g, 4.38 mmol), HOBT (0.89 g, 5.83 mmol) and N-ethylmorpholine (0.92 ml, 7.29 mmol) were added to a solution of 2-{[(4-fluorophenyl)methyl]oxy}-5-formylbenzoic acid (may be prepared by Description 105; 1 g, 3.65 mmol) in N,N-dimethylformamide (25 ml), and the mixture was stirred at room temperature for 4 hrs. The N,N-dimethylformamide was evaporated under reduced pressure on a buchi. Saturated aqueous sodium hydrogen carbonate (50 ml) and ethyl acetate (100 ml) were added to the residue and the mixture was stirred for 30 mins. The organics were separated and washed with water (50 ml), dried (MgSO4) and evaporated under reduced pressure to yield the title compound as a pale yellow solid. No further purification. No further purification carried out. 0.98 g.

Workup

  1. customThe N,N-dimethylformamide was evaporated under reduced pressure on a buchi
  2. additionSaturated aqueous sodium hydrogen carbonate (50 ml) and ethyl acetate (100 ml) were added to the residue
  3. stirringthe mixture was stirred for 30 mins
  4. customThe organics were separated
  5. washwashed with water (50 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9a47b3305e5f4129b7b72906497a1e99
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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