Acetic Acid → HCID 73051331, compound

HRID 1048708Notes

Reaction equation

HRID 1048708 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([C:9]#[C:10][C:11]2[N:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]3=[N:13][C:12]=2[CH2:20][NH:21][C:22](=[O:34])[NH:23][C:24]2[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=2)[C:27]([O:29]C)=[O:28])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].C(O)(=O)C>CO.O1CCCC1.O>[F:36][C:2]([F:1])([F:35])[C:3]1[CH:4]=[C:5]([C:9]#[C:10][C:11]2[N:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]3=[N:13][C:12]=2[CH2:20][NH:21][C:22](=[O:34])[NH:23][C:24]2[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=2)[C:27]([OH:29])=[O:28])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 118195064HCID 118195064, compound

Product 1

HCID 73051331HCID 73051331, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

0.038 g (0.078 mmol) of methyl 3-(3-((3-((3-(trifluoromethyl)phenyl)ethynyl) imidazo[1,2-a]pyridin-2-yl)methyl)ureido)benzoate were dissolved in 2 ml of a methanol/tetrahydrofurane mixture (1/1, v/v) with magnetic stirring and then 0.931 ml (0.931 mmol) of a (1M) NaOH aqueous solution were added and the mixture was stirred at r.t. for 16 h before being treated with a solution of 0.053 ml (0.931 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 0.026 g (yield=70%) of 3-(3-((3-((3-(trifluoromethyl)phenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)methyl) ureido) benzoic acid as a white solid. LC-MS: m/z=479 (MH+); UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 12.83 (s, 1H), 8.96 (s, 1H), 8.73 (d, J=6.7 Hz, 1H), 8.04 (s, 2H), 7.90 (d, J=7.5 Hz, 1H), 7.69 (dd, J=13.0, 8.4 Hz, 2H), 7.58 (d, J=7.7 Hz, 2H), 7.45 (d, J=7.5 Hz, 2H), 7.29 (t, J=7.9 Hz, 1H), 7.13 (t, J=6.8 Hz, 1H), 6.80 (t, J=5.4 Hz, 1H), 4.62 (d, J=5.6 Hz, 2H).

Workup

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

Sources & evidence

ORD record
ord-e783731b6c63447eb541998201f96046
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

Loading…