1,2-Dichloroethane → HCID 67106849, compound

HRID 1623821Notes

Reaction equation

HRID 1623821 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N1CCOCC1)C.[Br:30][C:31]1[CH:32]=[CH:33][C:34]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][C:45]([F:48])=[CH:44][C:43]=2[F:49])=[C:35]([CH:39]=1)[C:36](O)=[O:37]>CN(C)C=O>[Br:30][C:31]1[CH:32]=[CH:33][C:34]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][C:45]([F:48])=[CH:44][C:43]=2[F:49])=[C:35]([CH:39]=1)[C:36]([NH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)=[O:37]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 7525EthylmorpholineHCID 100093-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 62196689HCID 62196689, compound

Product 1

HCID 67106849HCID 67106849, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Pyridinamine (0.21 g, 2.19 mmol), EDC (0.34 g, 1.75 mmol), HOBT (0.36 g, 2.33 mmol) and N-ethylmorpholine (0.37 ml, 2.91 mmol) were added to a solution of 5-bromo-2-{[(2,4-difluorophenyl)methyl]oxy}benzoic acid (may be prepared by Description 103; 0.5 g, 1.46 mmol) in N,N-dimethylformamide (25 ml), and the mixture was stirred at room temperature for 4 hours. The N,N-dimethylformamide was removed on a buchi and the residue was diluted with ethyl acetate (50 ml) washed with saturated aqueous sodium hydrogencarbonate (1×25 ml) and water (1×25 ml) and dried (MgSO4), filtered and evaporated to yield the title compound as a white solid. 0.6 g.

Workup

  1. customThe N,N-dimethylformamide was removed on a buchi
  2. additionthe residue was diluted with ethyl acetate (50 ml)
  3. washwashed with saturated aqueous sodium hydrogencarbonate (1×25 ml) and water (1×25 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0840736c7f9049a0b2b2520c018339d1
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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