Sodium Chloride → HCID 90032105, compound

HRID 1048722Notes

Reaction equation

HRID 1048722 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]2[C:11]=1[C:12]#[C:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH:20][C:21]1[CH:22]=[C:23]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:24]=[CH:25][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Na+].[Cl-]>CN(C)C=O>[C:14]1([C:13]#[C:12][C:11]2[N:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]3=[N:4][C:3]=2[CH2:2][O:20][C:21]2[CH:22]=[C:23]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:24]=[CH:25][CH:26]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 10796Cesium carbonateHCID 836758N-(3-hydroxyphenyl)methanesulfonamideHCID 90031616HCID 90031616, compound

Product 1

HCID 90032105HCID 90032105, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

0.094 g (0.352 mmol) of 2-(chloromethyl)-3-(phenylethynyl)imidazo[1,2-a]pyridine were dissolved in 2 ml of dimethylformamide with magnetic stirring, 121 mg (0.529 mmol) of N-(3-hydroxyphenyl)methanesulfonamide and 0.172 g (0.529 mmol) of cesium carbonate were added. The mixture was stirred at 60° C. for 3 h before being poured onto 15 ml of a saturated NaCl aqueous solution. The aqueous phase was extracted with 2×20 ml of ethyl acetate. The combined organic phases were dried on Na2SO4 which was then removed by filtration. The obtained filtrate was concentrated in vacuo. The crude residue was purified by preparative HPLC and 0.028 g (yield=18%) of N-(3-((3-(phenylethynyl)imidazo[1,2-a]pyridin-2-yl)-methoxy)phenyl)methane sulfonamide were obtained as a white solid. LC-MS: m/z=418 (MH+); UV purity at 254 nm=95%. 1H NMR (300 MHz, DMSO) δ 9.53 (s, 1H), 8.55 (d, J=6.8 Hz, 1H), 7.76-7.57 (m, 3H), 7.54-7.33 (m, 4H), 7.17-7.02 (m, 2H), 6.89 (dd, J=8.0, 1.1 Hz, 1H), 6.79 (t, J=2.1 Hz, 1H), 6.69-6.54 (m, 1H), 5.07 (s, 2H), 3.14 (s, 3H).

Workup

  1. additionwere added
  2. extractionThe aqueous phase was extracted with 2×20 ml of ethyl acetate
  3. customThe combined organic phases were dried on Na2SO4 which
  4. customwas then removed by filtration
  5. concentrationThe obtained filtrate was concentrated in vacuo
  6. customThe crude residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-3f0da7abbd0942c792248ff0e7fc9fd2
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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