Hydrochloric Acid → 1-{4-[(ethylamino)carbonyl]-2-hydroxyphenyl}-N-cyclopropyl-1H-1,2,3-triazole-4-carboxamide

HRID 1717342Notes

Reaction equation

HRID 1717342 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[C:15]([C:17]([O:19]CC)=O)[N:14]=[N:13]2)=[C:8]([OH:22])[CH:7]=1)=[O:5])[CH3:2].[CH:23]1([NH2:26])[CH2:25][CH2:24]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.O.C(N(CC)CC)C>[CH:23]1([NH:26][C:17]([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][C:8]=3[OH:22])[CH:16]=2)=[O:19])[CH2:25][CH2:24]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68517012ethyl 1-{4-[(ethylamino)carbonyl]-2-hydroxyphenyl}-1H-1,2,3-triazole-4-carboxylate

Product 1

HCID 576650001-{4-[(ethylamino)carbonyl]-2-hydroxyphenyl}-N-cyclopropyl-1H-1,2,3-triazole-4-carboxamideYield 59%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

The product obtained in the same manner as in Example 133e) from ethyl 1-{4-[(ethylamino)carbonyl]-2-hydroxyphenyl}-1H-1,2,3-triazole-4-carboxylate (2.37 g) obtained in Example 133c) was dissolved in DMF (18 ml), cyclopropylamine (0.51 ml), triethylamine (1.01 ml), HOBt (1.12 g) and WSC (1.40 g) were successively added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was acidified with 1N hydrochloric acid. The precipitated crystals were collected by filtration and washed with water to give the title compound as a pale-brown powder (1.41 g, yield in 2 steps 59%).

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-e111487706fe4c048955a971fb376e2c
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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