Hydrochloric Acid → (5Z)-5-({1-[4-chloro-2-(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-3-(2,3-dihydroxypropyl)-1,3-thiazolidine-2,4-dione

HRID 2400793Notes

Reaction equation

HRID 2400793 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12](/[CH:16]=[C:17]4/[C:18](=[O:31])[N:19]([CH2:23][CH:24]5[CH2:28][O:27]C(C)(C)[O:25]5)[C:20](=[O:22])[S:21]/4)=[CH:13][CH:14]=3)[CH:9]=[N:8]2)=[C:4]([C:34]([F:37])([F:36])[F:35])[CH:3]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12](/[CH:16]=[C:17]4/[C:18](=[O:31])[N:19]([CH2:23][CH:24]([OH:25])[CH2:28][OH:27])[C:20](=[O:22])[S:21]/4)=[CH:13][CH:14]=3)[CH:9]=[N:8]2)=[C:4]([C:34]([F:36])([F:35])[F:37])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58530891HCID 58530891, compound

Product 1

HCID 58530742(5Z)-5-({1-[4-chloro-2-(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-3-(2,3-dihydroxypropyl)-1,3-thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
45 °C

Procedure

A solution of (5Z)-5-({1-[4-chloro-2-(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-1,3-thiazolidine-2,4-dione (Example 42; 0.1 mmol) in dioxane (3 mL) was treated with 10% aq. HCl (0.5 mL) and stirred at 45° C. overnight. Concentration of the reaction in vacuo gave a pale yellow solid which was triturated with ether to afford pure (5Z)-5-({1-[4-chloro-2-(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-3-(2,3-dihydroxypropyl)-1,3-thiazolidine-2,4-dione as a pale yellow crystalline solid.

Workup

  1. customConcentration of the reaction in vacuo
  2. customgave a pale yellow solid which
  3. customwas triturated with ether

Sources & evidence

ORD record
ord-00f44d41fbd946ada6b82ac1faef0b1f
Source dataset
uspto-grants-2014_08
Patent number
US08796256B2

Reaction notes

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