Sodium Hydroxide → 4-(5-Bromo-2-(thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)benzoic acid

HRID 1806114Notes

Reaction equation

HRID 1806114 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([S:19][C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=2)[C:6]([NH:9][C:10]2[S:11][C:12]3[C:17]([N:18]=2)=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:7][CH:8]=1.[OH-].[Na+]>CO>[Br:2][C:3]1[CH:4]=[C:5]([S:19][C:20]2[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=2)[C:6]([NH:9][C:10]2[S:11][C:12]3[C:17]([N:18]=2)=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86631508Methyl 4-(5-bromo-2-(thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)benzoate hydrochloride

Product 1

HCID 577425984-(5-Bromo-2-(thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)benzoic acidYield 70.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Heated a mixture of methyl 4-(5-bromo-2-(thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)benzoate hydrochloride (0.570 g, 1.12 mmol), 1N aqueous sodium hydroxide (2.80 mL, 2.80 mmol), and methanol (6 mL) at 65° C. for an hour. Cooled, and partitioned between saturated NH4Cl (30 mL), 1N HCl (3 mL), water (10 mL) and chloroform. The mixture was filtered, washed with water, and dried to afford the title compound (0.360 g, 70.1% yield). 1H NMR (d6-DMSO) δ 7.35 (dd, 1H), 7.43 (d, 2H), 7.50 (s, 1H), 7.67 (d, 1H), 7.94 (d, 2H), 8.44 (s, 1H).

Workup

  1. temperatureHeated
  2. temperatureCooled
  3. custompartitioned between saturated NH4Cl (30 mL), 1N HCl (3 mL), water (10 mL) and chloroform
  4. filtrationThe mixture was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-e7c30e227ef64162abf79e521066d98f
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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