Hydrochloric Acid → 2-(4-Isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-8-carboxylic acid

HRID 1190275Notes

Reaction equation

HRID 1190275 reaction equation
C[O:2][C:3]([C:5]1[CH:26]=[CH:25][C:8]2[C:9]3[N:10]=[C:11]([C:17]4[N:21]([CH:22]([CH3:24])[CH3:23])[CH:20]=[N:19][N:18]=4)[S:12][C:13]=3[CH2:14][CH2:15][O:16][C:7]=2[CH:6]=1)=[O:4].[OH-].[Li+].Cl>C1COCC1.O>[CH:22]([N:21]1[CH:20]=[N:19][N:18]=[C:17]1[C:11]1[S:12][C:13]2[CH2:14][CH2:15][O:16][C:7]3[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:26]=[CH:25][C:8]=3[C:9]=2[N:10]=1)([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 582040372-(4-isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-8-carboxylic acid methyl ester

Product 1

HCID 582037112-(4-Isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-8-carboxylic acidYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-(4-isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-8-carboxylic acid methyl ester in THF (6 mL) and water (1.5 mL) was added an aqueous 1N lithium hydroxide solution (1.0 mL, 1.0 mmol). The reaction mixture was stirred for 65 hours then an aqueous 1N HCl solution (2 mL) was added and the mixture was concentrated in vacuo to remove THF. A small quantity of MeOH was added to the resultant mixture and the solid was collected by filtration to give the title compound as an off-white solid (226 mg, 95%). LCMS: RT=3.88 min, [M+H]+=357

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customto remove THF
  3. additionA small quantity of MeOH was added to the resultant mixture
  4. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-d0626b8dab6244ef97b969ddd7ae1d21
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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