Hydrochloric Acid → HCID 66552472, compound

HRID 1615872Notes

Reaction equation

HRID 1615872 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([C:11]1[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=1)[C:14]([O:16]CC)=[O:15])[N:5]=2.C1COCC1.O.[OH-].[Li+].Cl>O.CO>[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([C:11]1[CH:12]=[C:13]([CH:19]=[CH:20][CH:21]=1)[C:14]([OH:16])=[O:15])[N:5]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 66552469HCID 66552469, compound

Product 1

HCID 66552472HCID 66552472, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 3-(2-aminothiazolo[5,4-b]pyridin-5-yl)benzoate (400 mg, 1.34 mmol) in a mixture of water (2.0 mL), THF (2.0 mL) and methanol (2.0 mL) was added lithium hydroxide monohydrate (281 mg, 11.85 mmol). The reaction mixture was stirred at room temperature for 16 h and was neutralized with 1N aqueous HCl until pH=6 (monitored with pH paper). The organic solvent was removed in vacuo and the resulting brown solid was collected and dried to give 310 mg (85% yield) of 3-(2-aminothiazolo[5,4-b]pyridin-5-yl)benzoic acid.

Workup

  1. customThe organic solvent was removed in vacuo
  2. customthe resulting brown solid was collected
  3. customdried

Sources & evidence

ORD record
ord-f5454e5d40144a16b404b37d40bfcbad
Source dataset
uspto-grants-2014_07
Patent number
US08765747B2

Reaction notes

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