1,2-Dichloroethane → HCID 86668212, compound

HRID 1623820Notes

Reaction equation

HRID 1623820 reaction equation
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N1CCOCC1)C.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([NH2:29])[CH: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:25]2[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=2)=[O:43])[CH:34]=[CH:35][C:36]=1[F:37]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 7525EthylmorpholineHCID 100093-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 86668204HCID 86668204, compound

Product 1

HCID 86668212HCID 86668212, 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 3-pyridinamine (0.48 g, 5.13 mmol) were added to a solution of 2-{[(3,4-difluorophenyl)methyl]oxy}-5-formylbenzoic acid (may be prepared as described in Description 101; 1 g, 3.42 mmol) in N,N-dimethylformamide (25 ml), and the mixture was stirred at room temperature. The N,N-dimethylformamide was evaporated under reduced pressure and the residue was diluted with ethyl acetate (100 ml). The organic layer was 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 yellow solid. 1.19 g.

Workup

  1. customThe N,N-dimethylformamide was evaporated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate (100 ml)
  3. washThe organic layer was 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-94760c0049114289a7e9eb5dbe267415
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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