Sodium Hydroxide → HCID 57665151, compound

HRID 1717422Notes

Reaction equation

HRID 1717422 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([O:17][CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:15]([C:27]([O:29]C)=O)[N:14]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[OH-].[Na+].[CH:33]1([NH2:36])[CH2:35][CH2:34]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CO>[CH:33]1([NH:36][C:27]([C:15]2[N:14]=[N:13][N:12]([C:9]3[CH:10]=[CH:11][C:6]([C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=3)[C:16]=2[O:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:29])[CH2:35][CH2:34]1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68517435HCID 68517435, compound

Product 1

HCID 57665151HCID 57665151, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 1-{4-[(ethylamino)carbonyl]phenyl}-5-(3-phenylpropoxy)-1H-1,2,3-triazole-4-carboxylate (106 mg, 0.26 mmol) obtained in Example 1211b) in methanol (3 ml) was added 1N sodium hydroxide (1 ml), the mixture was stirred at 60° C. for 30 min, and the solvent was evaporated. The residue was adjusted to pH 2-3 with 1N hydrochloric acid. The precipitated crystals were collected by filtration, dried and dissolved in DMF (3 ml). Cyclopropylamine (15 mg, 0.26 mmol), HOBt (44 mg, 0.26 mmol) and WSC (55 mg, 0.29 mmol) were successively added, and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate) to give the title compound as a white powder (88 mg, 78%).

Workup

  1. customthe solvent was evaporated
  2. filtrationThe precipitated crystals were collected by filtration
  3. customdried
  4. dissolutiondissolved in DMF (3 ml)
  5. stirringthe reaction mixture was stirred at room temperature overnight
  6. customThe solvent was evaporated under reduced pressure
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. washwashed with saturated aqueous sodium hydrogen carbonate solution
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate)

Sources & evidence

ORD record
ord-602e9bd36fe8478cb6bad949a43aa821
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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