Acetic Acid → HCID 72721009, compound

HRID 1048724Notes

Reaction equation

HRID 1048724 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:19]#[C:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)=[C:9]([CH2:11][S:12][CH2:13][C:14]([O:16]CC)=[O:15])[N:10]=2)[CH:7]=1.C(O)C.[OH-].[Na+].C(O)(=O)C>O.O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:19]#[C:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:29])([F:28])[F:30])[CH:22]=3)=[C:9]([CH2:11][S:12][CH2:13][C:14]([OH:16])=[O:15])[N:10]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 73052445HCID 73052445, compound

Product 1

HCID 72721009HCID 72721009, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

16 g (35.3 mmol) of ethyl 2-((6-chloro-3-((3-(trifluoromethyl)phenyl)ethynyl) imidazo[1,2-a]pyridin-2-yl)methylthio)acetate were added to 75 ml of ethanol and 75 ml of tetrahydrofurane before adding 4.24 ml (42.4 mmol) of a 32% sodium hydroxide aqueous solution. The mixture was stirred at r.t. for 2 h, and then 50 ml of water were added after 30 min for solubilising the precipitated solid. The solvent was evaporated in vacuo, the obtained residue was diluted in 250 ml of water and 50 ml of diisopropyl ether, and then the solution was brought to an acid pH by adding 2.53 ml (44.2 mmol) of acetic acid. The precipitated solid was filtered and then washed with water and diisopropyl ether. 12.45 g (yield=83%) of 2-((6-chloro-3-((3-(trifluoromethyl)phenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)methylthio)acetic acid was obtained as a yellow solid. LC-MS: m/z=425 (MH+) UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 12.65 (s, 1H), 8.96 (s, 1H), 8.19 (s, 1H), 8.03 (d, J=7.6 Hz, 1H), 7.84-7.63 (m, 3H), 7.50 (dd, J=9.5, 1.8 Hz, 1H), 4.07 (s, 2H), 3.40 (s, 2H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionthe obtained residue was diluted in 250 ml of water
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water and diisopropyl ether

Sources & evidence

ORD record
ord-6591f034cdb241469a4b6fc4c2c1a2df
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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