Sodium Hydroxide → HCID 57665106, compound

HRID 1717424Notes

Reaction equation

HRID 1717424 reaction equation
[CH2:1]([O:3][C:4]1[N:8]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([NH:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=2)[N:7]=[N:6][C:5]=1[C:20]([O:22]C)=O)[CH3:2].[OH-].[Na+].[CH:26]1([NH2:29])[CH2:28][CH2:27]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CO>[CH:26]1([NH:29][C:20]([C:5]2[N:6]=[N:7][N:8]([C:9]3[CH:10]=[CH:11][C:12]([C:15]([NH:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:14]=3)[C:4]=2[O:3][CH2:1][CH3:2])=[O:22])[CH2:28][CH2:27]1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68516392HCID 68516392, compound

Product 1

HCID 57665106HCID 57665106, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 5-ethoxy-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxylate (159 mg, 0.5 mmol) obtained in Example 1212a) in methanol (5 ml) was added 1N sodium hydroxide (2 ml) and the mixture was stirred at 60° C. for 30 min. The solvent was evaporated, and the residue was adjusted to pH 2-3 with 1N hydrochloric acid. The precipitated crystals were collected by filtration, dried and dissolved in DMF (5 ml). Cyclopropylamine (29 mg, 0.5 mmol), HOBt (84 mg, 0.55 mmol) and WSC (105 mg, 0.55 mmol) were successively added, and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, water (5 ml) was added to the residue, and the precipitated crystals were collected by filtration and dried to give the title compound as a white powder (140 mg, 82%).

Workup

  1. customThe solvent was evaporated
  2. filtrationThe precipitated crystals were collected by filtration
  3. customdried
  4. dissolutiondissolved in DMF (5 ml)
  5. stirringthe reaction mixture was stirred at room temperature overnight
  6. customThe solvent was evaporated under reduced pressure, water (5 ml)
  7. additionwas added to the residue
  8. filtrationthe precipitated crystals were collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-9ac73403db3745298b37ae49f4766e15
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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