Hydrochloric Acid → HCID 67521133, compound

HRID 1926373Notes

Reaction equation

HRID 1926373 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=2)[O:11][CH2:12][C:13]([O:15]C)=[O:14])=[CH:4][C:3]=1[C:20]1[S:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=1.[OH-].[Na+].Cl>CCO.O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=2)[O:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:4][C:3]=1[C:20]1[S:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67520661HCID 67520661, compound

Product 1

HCID 67521133HCID 67521133, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of methyl 3-[6-amino-5-(1,3-benzothiazol-2-yl)pyridin-3-yl]phenoxyacetate (75 mg, 0.19 mmol) in EtOH (4.0 mL) and H2O (4.0 mL) was added 3M aqueous NaOH (0.30 mL, 1.0 mmol). The reaction mixture was left to stir at rt overnight. Then, the mixture was acidified with 1M HCl aqueous to pH=2. Vacuum filtration afforded the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=4.80 (s, 2H), 6.93 (dd, J=7.7, 2.1 Hz, 1H), 7.25-7.29 (m, 1H), 7.31 (d, J=7.8 Hz, 1H), 7.40 (t, J=7.8 Hz, 1H), 7.48-7.54 (m, 1H), 7.55-7.62 (m, 1H), 8.15 (dd, J=18.4, 7.6 Hz, 2H), 8.31 (d, J=2.0 Hz, 1H), 8.55 (d, J=2.3 Hz, 1H), 13.06 (br. s., 1H). MS (ES+): m/z=378.07 (100) [MH+]. HPLC: tR=3.50 min (ZQ3, polar—5 min).

Workup

  1. waitThe reaction mixture was left
  2. filtrationVacuum filtration

Sources & evidence

ORD record
ord-e1c175a326774938aa9d755b9e1a9cea
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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