1,2-Dichloroethane → HCID 86668208, compound

HRID 1623822Notes

Reaction equation

HRID 1623822 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.[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:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[O:42])=[CH:33][CH:32]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 7525EthylmorpholineHCID 100093-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 86668206HCID 86668206, compound

Product 1

HCID 86668208HCID 86668208, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Pyridinamine (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 h. The N,N-dimethylformamide was evaporated 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 min. 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 was carried out. 1.23 g.

Workup

  1. customThe N,N-dimethylformamide was evaporated 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 min
  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-dd928de8ff3148b2a18a665e6a576a1f
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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