Water → {2,6-Dimethyl-5-[(4,5,7-Trifluoro-1,3-Benzothiazol-2-Yl)methyl]pyridin-3-Yl}acetic Acid

HRID 900968Notes

Reaction equation

HRID 900968 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8]C#N)=[CH:6][C:5]([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)=[C:4]([CH3:24])[N:3]=1.O.[C:26]([O-:29])(O)=[O:27].[Na+]>Cl>[CH3:1][C:2]1[C:7]([CH2:8][C:26]([OH:29])=[O:27])=[CH:6][C:5]([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)=[C:4]([CH3:24])[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 689391512,6-Dimethyl-5-(4,5,7-trifluorobenzothiazole-2-yl-methyl)-pyridin-3-yl-acetonitrile

Product 1

HCID 10150300{2,6-Dimethyl-5-[(4,5,7-Trifluoro-1,3-Benzothiazol-2-Yl)methyl]pyridin-3-Yl}acetic AcidYield 75%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2,6-dimethyl-5-(4,5,7-trifluorobenzothiazole-2-yl-methyl)-pyridin-3-yl-acetonitrile (0.50 g, 1.43 mmol) in 50% hydrochloric acid (HCl) (8 ml, 0.2 M) under nitrogen is warmed (90° C. bath) and stirred overnight. The reaction mixture is added to H2O (20 mL) and brought to pH 5 with NaHCO3. The solids are filtered and the aqueous extracted with ethyl acetate (5×30 mL). The solid and extracts are combined and purified by reverse-phase HPLC (acetonitrile/water, 0.05% HCl)to give 2,6-Dimethyl-5-(4,5,7-trifluoro-benzothiazole-2-ylmethyl)-pyridin-3-yl-acetic acid as a white solid (0.40 g, 75%): mp 211° C. dec 1H NMR (DMSO-d6, 300 MHz) δ 8.29 (s, 1 H), 7.85-7.74 (m, 1 H), 4.80 (s, 2 H), 3.86 (s, 2 H), 2.73 (s, 3 H), 2.67 (s, 3 H), ESI-LCMS m/z calcd for C17H13F3N2O2S: 366.1; found 367.0 (M+1)+. Anal. Calcd for C17H14ClF3N2O2S: C, 50.69; H, 3.50; N, 6.95; Cl, 8.80; S; 7.96. Found: C, 50.48; H, 3.63; N, 6.89; Cl, 8.97; S, 7.84.

Workup

  1. filtrationThe solids are filtered
  2. extractionthe aqueous extracted with ethyl acetate (5×30 mL)
  3. custompurified by reverse-phase HPLC (acetonitrile/water, 0.05% HCl)

Sources & evidence

ORD record
ord-16b3eaa6d462452983fb734835e4bf99
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Reaction notes

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