1,2-Dichloroethane → HCID 69936822, compound

HRID 1623779Notes

Reaction equation

HRID 1623779 reaction equation
[CH:1]1[CH:2]=C[C:4]2[N:9](O)N=[N:7][C:5]=2[CH:6]=1.[N:11]1([C:17]([C:19]2[CH:20]=[CH:21][C:22]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:23]([CH:27]=2)[C:24]([OH:26])=O)=[O:18])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.N1C=CC=C(N)C=1.C(Cl)CCl>CN(C)C=O.O>[N:11]1([C:17]([C:19]2[CH:20]=[CH:21][C:22]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:23]([CH:27]=2)[C:24]([NH:7][C:5]2[CH:4]=[N:9][CH:2]=[CH:1][CH:6]=2)=[O:26])=[O:18])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 100093-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 67107404HCID 67107404, compound

Product 1

HCID 69936822HCID 69936822, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Neat HOBT (90 mg, 0.59 mmol) was added in one charge to a stirred solution of 5-(4-morpholinylcarbonyl)-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 57; 200 mg, 0.59 mmol), 3-pyridinamine (55.1 mg, 0.59 mmol) and EDC (112 mg, 0.59 mmol) in N,N-dimethylformamide (5 ml) under nitrogen at room temperature. The reaction mixture was stirred at room temperature for 4 h. The mixture was diluted with water (50 ml) and extracted with ethyl acetate (3×50 ml). The organic phase was washed with sodium hydroxide solution (1 mol/l, 25 ml), saturated brine (25 ml), dried over sodium sulfate, and evaporated in vacuo to give the crude product. The crude product was washed with ether (5 ml) and dried to yield the title compound as a white solid. 67 mg.

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. washThe organic phase was washed with sodium hydroxide solution (1 mol/l, 25 ml), saturated brine (25 ml)
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customto give the crude product
  6. washThe crude product was washed with ether (5 ml)
  7. customdried

Sources & evidence

ORD record
ord-ab2580fc05c04df6abdef3969ec65cd6
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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