Hydrochloric Acid → HCID 86664081, compound

HRID 1615871Notes

Reaction equation

HRID 1615871 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[S:8][C:9]3[C:14]([N:15]=2)=[CH:13][CH:12]=[C:11]([C:16]2[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=2)[C:19]([O:21]CC)=[O:20])[N:10]=3)=[O:5])[CH2:3][CH2:2]1.O.[OH-].[Li+].Cl>O.C1COCC1.CO>[CH:1]1([C:4]([NH:6][C:7]2[S:8][C:9]3[C:14]([N:15]=2)=[CH:13][CH:12]=[C:11]([C:16]2[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=2)[C:19]([OH:21])=[O:20])[N:10]=3)=[O:5])[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86664082HCID 86664082, compound

Product 1

HCID 86664081HCID 86664081, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-(2-(cyclopropanecarboxamido)thiazolo[5,4-b]pyridin-5-yl)benzoate (870 mg, 2.37 mmol) was dissolved in the mixture of water (3.0 mL), THF (3.0 mL) and methanol (3.0 mL) followed by the addition of lithium hydroxide monohydrate (497 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). Upon removal of the organic solvent in vacuo the resulting brown solid was collected and dried to give 620 mg (87% yield) of 3-(2-(cyclopropanecarboxamido)thiazolo[5,4-b]pyridin-5-yl)benzoic acid.

Workup

  1. customUpon removal of the organic solvent in vacuo the resulting brown solid
  2. customwas collected
  3. customdried

Sources & evidence

ORD record
ord-2b77fd12d913437c9ed1a85989e95636
Source dataset
uspto-grants-2014_07
Patent number
US08765747B2

Reaction notes

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