Hydrochloric Acid → 4-[6-Amino-5-(1,3-benzothiazol-2-yl)pyridin-3-yl]phenoxyacetic acid

HRID 1926375Notes

Reaction equation

HRID 1926375 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:20]=[CH:19][C:11]([O:12][CH2:13][C:14]([O:16]CC)=[O:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:21]1[S:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1.[OH-].[Na+].Cl>CCO>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:20]=[CH:19][C:11]([O:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:21]1[S:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67520764Ethyl 4-[6-amino-5-(1,3-benzothiazol-2-yl)pyridin-3-yl]phenoxyacetate

Product 1

HCID 675208764-[6-Amino-5-(1,3-benzothiazol-2-yl)pyridin-3-yl]phenoxyacetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of ethyl 4-[6-amino-5-(1,3-benzothiazol-2-yl)pyridin-3-yl]phenoxyacetate (132 mg, 0.330 mmol) in EtOH (2.0 mL) was added 3M aqueous NaOH (0.50 mL, 1.5 mmol). Then, the mixture was acidified to pH=2 with 1M aq. HCl. Vacuum filtration afforded the title compound as a yellow solid. MS (ES+): m/z=506.88 (100) [MH+]. HPLC: tR=3.14 min (ZQ3, polar—5 min).

Workup

  1. filtrationVacuum filtration

Sources & evidence

ORD record
ord-4248f6e0300342a3ac1d33fbea0aa561
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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