1,2-Dichloroethane → HCID 86668211, compound

HRID 1623819Notes

Reaction equation

HRID 1623819 reaction equation
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N1CCOCC1)C.[N:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][N:24]=1.[F:30][C:31]1[CH:32]=[C:33]([CH2:38][O:39][C:40]2[CH:48]=[CH:47][C:46]([CH:49]=[O:50])=[CH:45][C:41]=2[C:42](O)=[O:43])[CH:34]=[CH:35][C:36]=1[F:37]>CN(C)C=O>[F:30][C:31]1[CH:32]=[C:33]([CH2:38][O:39][C:40]2[CH:48]=[CH:47][C:46]([CH:49]=[O:50])=[CH:45][C:41]=2[C:42]([NH:29][C:26]2[CH:27]=[CH:28][N:23]=[N:24][CH:25]=2)=[O:43])[CH:34]=[CH:35][C:36]=1[F:37]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 2984924-AminopyridazineHCID 86668204HCID 86668204, compound

Product 1

HCID 86668211HCID 86668211, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (0.79 g, 4.11 mmol), HOBT (0.84 g, 5.48 mmol), N-ethylmorpholine (0.87 mL, 6.84 mmol) and 4-pyridazinamine (0.49 g, 5.13 mmol) were added to a solution of 2-{[(3,4-difluorophenyl)methyl]oxy}-5-formylbenzoic acid (may be prepared by Description 101; 1 g, 3.42 mmol) in N,N-dimethylformamide (DMF; 25 ml) and the mixture was stirred at room temperature. The DMF was evaporated under reduced pressure and the residue was diluted with ethyl acetate (100 ml) and the organic layer washed with saturated sodium hydrogencarbonate (2×50 ml) and water (2×50 ml). The organic layer was dried (MgSO4), filtered and evaporated under reduced pressure to yield the title compound as a dark yellow solid. 0.98 g.

Workup

  1. customThe DMF was evaporated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate (100 ml)
  3. washthe organic layer washed with saturated sodium hydrogencarbonate (2×50 ml) and water (2×50 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-da4654ef39104e4a9fff88fef8b34748
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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