Hydrochloric Acid → 4-[1-(6-Quinolinylmethyl)-1H-1,2,3-triazolo[4,5-b]pyrazin-6-yl]-1H-pyrazole-1-acetic acid

HRID 16021Notes

Reaction equation

HRID 16021 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[N:11]=[C:12]3[N:18]([CH2:19][C:20]4[CH:21]=[C:22]5[C:27](=[CH:28][CH:29]=4)[N:26]=[CH:25][CH:24]=[CH:23]5)[N:17]=[N:16][C:13]3=[N:14][CH:15]=2)[CH:7]=[N:6]1.[Li+].[OH-].Cl>CO.O>[N:26]1[C:27]2[C:22](=[CH:21][C:20]([CH2:19][N:18]3[C:12]4[C:13](=[N:14][CH:15]=[C:10]([C:8]5[CH:7]=[N:6][N:5]([CH2:4][C:3]([OH:30])=[O:2])[CH:9]=5)[N:11]=4)[N:16]=[N:17]3)=[CH:29][CH:28]=2)[CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59341942HCID 59341942, compound

Product 1

HCID 593418254-[1-(6-Quinolinylmethyl)-1H-1,2,3-triazolo[4,5-b]pyrazin-6-yl]-1H-pyrazole-1-acetic acidYield 56.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of [4-(3-quinolin-6-ylmethyl-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)-pyrazol-1-yl]-acetic acid methyl ester (242 mgs, 0.60 mmol) in MeOH (4 mL) was added a freshly prepared solution of LiOH (72 mgs, 3.02 mmol) in water (1 mL). The reaction was stirred for 16 hours at ambient temperature. The white suspension was then neutralized to pH 7 with 1 N HCl, and a white solid precipitated out. The solid was filtered, washed with water, and dried under a high vacuum for 16 hours to afford [4-(3-quinolin-6-ylmethyl-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)-pyrazol-1-yl]-acetic acid (131 mgs, 56% yield).

Workup

  1. customa white solid precipitated out
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customdried under a high vacuum for 16 hours

Sources & evidence

ORD record
ord-eea52579a8194cc595b530c85a536032
Source dataset
uspto-grants-2010_06
Patent number
US07732604B2

Reaction notes

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