Hydrochloric Acid → 6-Ethyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl-acetic acid hydrochloride

HRID 900980Notes

Reaction equation

HRID 900980 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][C:5]1[CH:6]=[N:7][C:8]([CH2:24][CH3:25])=[C:9]([CH2:11][C:12]2[S:13][C:14]3[C:20]([F:21])=[CH:19][C:18]([F:22])=[C:17]([F:23])[C:15]=3[N:16]=2)[CH:10]=1.[OH-].[Na+].[ClH:29]>COCCOC.[Na+].[Cl-]>[ClH:29].[CH2:24]([C:8]1[N:7]=[CH:6][C:5]([CH2:4][C:3]([OH:26])=[O:2])=[CH:10][C:9]=1[CH2:11][C:12]1[S:13][C:14]2[C:20]([F:21])=[CH:19][C:18]([F:22])=[C:17]([F:23])[C:15]=2[N:16]=1)[CH3:25]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 596987776-Ethyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl-acetic acid-methyl ester

Product 1

HCID 689460236-Ethyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl-acetic acid hydrochlorideYield 80%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 6-ethyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl-acetic acid-methyl ester (0.27 g, 0.71 mmol) in DME (5 mL, 0.1 M) is cooled to 0° C. under nitrogen and treated with 0.4 M NaOH (3 mL, 1.2 mmol). After stirring for 2 h, the solution is acidified with 2 M HCl, diluted with saturated aq NaCl (10 mL), extracted with ethyl acetate (3×10 mL) and dried over Na2SO4. Purification by HPLC (acetonitrile/water, 0.05% HCl) provided 6-ethyl-5-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-pyridin-3-yl-acetic acid hydrochloride as a white solid (0.21 g, 80%): mp 220° C. dec; Rf 0.21 (10% methanol in dichloromethane), 1H NMR (DMSO-d6, 300 MHz) δ 8.60 (s, 1 H), 8.18 (br s, 1 H), 7.78 (ddd, J1=11.1 Hz, J2=9.6 Hz, J3=5.9 Hz, 1 H), 4.80 (s, 2 H), 3.79 (s, 2 H), 2.97 (q, J=7.6 Hz, 2 H), 1.20 (t, J=7.6 Hz, 3 H); ESI-LCMS m/z calcd for C17H13F3N2O2S: 366.1; found 367.0 (M+1)+. Anal. Calcd for C17H13F3N2O2S.HCl: C, 50.69; H, 3.50; N, 6.95; S, 7.96. Found: C, 55.41; H, 3.56; N, 6.91; S, 7.98.

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. dry with materialdried over Na2SO4
  3. customPurification by HPLC (acetonitrile/water, 0.05% HCl)

Sources & evidence

ORD record
ord-869c98c5389740009a3a0a1f364822b3
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Reaction notes

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