Hydrochloric Acid → HCID 16117588, compound

HRID 416598Notes

Reaction equation

HRID 416598 reaction equation
[N:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[S:3][C:2]=1[C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([NH:20][C:21](=[O:34])[C:22]2[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=2)[CH:19]=1)[C:13]([O:15]C)=[O:14].O.[OH-].[Na+].Cl>C1COCC1>[N:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[S:3][C:2]=1[C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([NH:20][C:21](=[O:34])[C:22]2[CH:23]=[C:24]([O:32][CH3:33])[C:25]([O:30][CH3:31])=[C:26]([O:28][CH3:29])[CH:27]=2)[CH:19]=1)[C:13]([OH:15])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 16117587HCID 16117587, compound

Product 1

HCID 16117588HCID 16117588, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-(thiazolo[5,4-c]pyridin-2-yl)-5-(3,4,5-trimethoxybenzamido)benzoate (80 mg, 0.167 mmol) was dissolved in 5 mL of THF and 2 mL of water containing 30 mg of sodium hydroxide. The reaction mixture was stirred at room temperature for 1 hour. It was then acidified to pH 4 with 6 N HCl and concentrated. The solids were collected by filtration and dried to afford 60 mg of 3-(thiazolo[5,4-c]pyridin-2-yl)-5-(3,4,5-trimethoxybenzamido)benzoic acid (78% yield) (MS, M++H=466).

Workup

  1. concentrationconcentrated
  2. filtrationThe solids were collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-6d552baad92e47f6beff774c9f1c7e96
Source dataset
uspto-grants-2012_01
Patent number
US08088928B2

Reaction notes

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