Acetic Acid → HCID 15654675, compound

HRID 1977373Notes

Reaction equation

HRID 1977373 reaction equation
C(O)(=O)C.[NH2:5][C:6]1[C:7]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]#[N:32])=[CH:21][CH:20]=2)=[C:8]([CH:14]=[CH:15][CH:16]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10].[C:33]([O-])([O-])([O-])[O:34][CH2:35][CH2:36][CH3:37]>>[C:31]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:17]2[C:7]3[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14][CH:15]=[CH:16][C:6]=3[N:5]=[C:33]2[O:34][CH2:35][CH2:36][CH3:37])=[CH:20][CH:21]=1)#[N:32]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 15654655Ethyl 3-amino-2-(((2'-cyano-[1,1'-biphenyl]-4-yl)methyl)amino)benzoateHCID 86586169Propyl orthocarbonate

Product 1

HCID 15654675HCID 15654675, compound

Conditions

Temperature
80 °C

Procedure

Acetic acid (0.2 g) was added to a solution of ethyl 3-amino-2-[(2′-cyanobiphenyl-4-yl)methyl]aminobenzoate (0.9 g) in propyl orthocarbonate (5 ml). The mixture was stirred at 80° C. for one hour. The reaction mixture was concentrated, and the concentrate was dissolved in ethyl acetate. The solution was washed with an aqueoues solution of sodium hydrogen carbonate. The solvent was evaporated to give crystals. Recrystallization from ethyl acetate-benzene afforded colorless crystals (0.72 g, 68%), m.p. 90-92° C. Elemental Analysis for C27H25N3O3:

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe concentrate was dissolved in ethyl acetate
  3. washThe solution was washed with an aqueoues solution of sodium hydrogen carbonate
  4. customThe solvent was evaporated
  5. customto give crystals
  6. customRecrystallization from ethyl acetate-benzene afforded colorless crystals (0.72 g, 68%), m.p. 90-92° C

Sources & evidence

ORD record
ord-31cce9c53ae54cb7ae2757770bc0f723
Source dataset
uspto-grants-2001_05
Patent number
US06232334B1

Reaction notes

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