Acetic Acid → HCID 73051476, compound

HRID 1048707Notes

Reaction equation

HRID 1048707 reaction equation
[CH3:1][N:2]([CH2:7][C:8]1[N:9]=[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]2[C:16]=1[C:17]#[C:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1)[CH2:3][C:4]([O-:6])=[O:5].CO.[OH-].[Na+].C(O)(=O)C>O.O1CCCC1>[CH3:1][N:2]([CH2:7][C:8]1[N:9]=[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]2[C:16]=1[C:17]#[C:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=1)[CH2:3][C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 131735992HCID 131735992, compound

Product 1

HCID 73051476HCID 73051476, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.22 g (0.543 mmol) of 2-(methyl((3-((3-(trifluoromethyl)phenyl) ethynyl) imidazo[1,2-a]pyridin-2-yl)methyl)amino)acetate were dissolved in 6 ml of a mixture consisting of methanol and tetrahydrofurane with magnetic stirring and then 0.543 ml (0.543 mmol) of a 1M NaOH aqueous solution were added. The mixture was stirred at r.t. for 16 h. 0.163 ml (0.163 mmol) of a 1M NaOH aqueous solution were added. The mixture was stirred at r.t. for a further 24 h before being treated with a solution of 0.04 ml (0.705 mmol) of acetic acid in 10 ml of water. The mixture was stirred at r.t. for 30 min. The solid formed was isolated by filtration, washed with 5 ml of water and dried in a vacuum bell jar in order to obtain 0.155 g (yield=73%) of 2-(methyl((3-((3-(trifluoromethyl)phenyl) ethynyl)imidazo[1,2-a]pyridin-2-yl)methyl)amino) acetic acid as a beige solid. LC-MS: m/z=388 (MH+); UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 8.74 (d, J=6.7 Hz, 1H), 8.10 (s, 1H), 7.97 (d, J=7.6 Hz, 1H), 7.77 (d, J=7.8 Hz, 1H), 7.74-7.64 (m, 2H), 7.49-7.39 (m, 1H), 7.13 (t, J=6.4 Hz, 1H), 4.02 (s, 2H), 3.59 (s, 1H), 3.33 (s, 2H), 2.41 (s, 3H).

Workup

  1. stirringThe mixture was stirred at r.t. for 16 h
  2. stirringThe mixture was stirred at r.t. for a further 24 h
  3. stirringThe mixture was stirred at r.t. for 30 min
  4. customThe solid formed
  5. customwas isolated by filtration
  6. washwashed with 5 ml of water
  7. customdried in a vacuum bell jar in order

Sources & evidence

ORD record
ord-49699e7a02b7489fa6ffd453884843e1
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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