Acetic Acid → HCID 15654675, compound

HRID 1737879Notes

Reaction equation

HRID 1737879 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 mi). 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 aqueous 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.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe concentrate was dissolved in ethyl acetate
  3. washThe solution was washed with an aqueous 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-141cf982425b448580577b4907eafa8d
Source dataset
uspto-grants-1999_10
Patent number
US05962491

Reaction notes

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