Acetic Acid → HCID 73052761, compound

HRID 1048725Notes

Reaction equation

HRID 1048725 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:21]#[C:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]([F:33])([F:32])[F:31])[CH:24]=3)=[C:9]([CH2:11][S:12]([CH2:15][C:16]([O:18]CC)=[O:17])(=[O:14])=[O:13])[N:10]=2)[CH:7]=1.[OH-].[Na+].O.C(O)(=O)C>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:21]#[C:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]([F:31])([F:32])[F:33])[CH:24]=3)=[C:9]([CH2:11][S:12]([CH2:15][C:16]([OH:18])=[O:17])(=[O:14])=[O:13])[N:10]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 73052604HCID 73052604, compound

Product 1

HCID 73052761HCID 73052761, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

100 mg (0.200 mmol) of ethyl 2-((6-chloro-3-((3-(trifluoromethoxy)phenyl)-ethynyl)imidazo[1,2-a]pyridin-2-yl)methylsulfonyl)acetate were dissolved in 2 ml of ethanol before adding 0.060 ml (0.599 mmol) of a 32% sodium hydroxide aqueous solution. The mixture was stirred at r.t. for 16 h. The solution was poured into 10 ml of water, acidified to an acid pH with acetic acid, extracted with 2×5 ml of dichloromethane, the combined organic phases were dried on Na2SO4 which was then removed by filtration and the obtained filtrate was concentrated in vacuo. 76 mg (yield=80%) of 2-((6-chloro-3-((3-(trifluoromethoxy)phenyl)ethynyl)-imidazo[1,2-a]pyridin-2-yl)methylsulfonyl)acetic acid were obtained as a yellow solid. LC-MS: m/z=473 (MH+) UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 14.72-12.20 (m, 1H), 9.00 (d, J=1.2 Hz, 1H), 7.88-7.76 (m, 3H), 7.62-7.45 (m, 3H), 4.96 (s, 2H), 4.42 (s, 2H).

Workup

  1. extractionextracted with 2×5 ml of dichloromethane
  2. customthe combined organic phases were dried on Na2SO4 which
  3. customwas then removed by filtration
  4. concentrationthe obtained filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5af1a2f52cba4b16b7600449d2c42d5c
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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