HCID 58387103, compound → HCID 178525973, compound

HRID 1045112Notes

Reaction equation

HRID 1045112 reaction equation
[Cl:1][C:2]1[C:3]([C:24]#[C:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:4][C:5]2[N:9]=[C:8]([O:10][CH2:11][C:12]([OH:14])=[O:13])[N:7](COCC[Si](C)(C)C)[C:6]=2[CH:23]=1>C(O)(C(F)(F)F)=O.O.CS(C)=O>[Cl:1][C:2]1[C:3]([C:24]#[C:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:4][C:5]2[N:9]=[C:8]([O:10][CH2:11][C:12]([OH:14])=[O:13])[NH:7][C:6]=2[CH:23]=1

Participants

4

Reactant 1

HCID 58387103HCID 58387103, compound2×

Product 1

HCID 178525973HCID 178525973, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 22392675Trifluoroacetic acid waterSolvent

Conditions

Temperature
65 °C

Procedure

In a 4 mL vial, [6-chloro-5-phenylethynyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yloxy]-acetic acid (compound 48-2, 79.0 mg, 0.173 mmol) was dissolved in 9:1 TFA/water (3 mL) and stirred at 65° C. for 10 min. The solution was then evaporated to dryness in vacuo to give brownish oil, which was dissolved in DMSO (1 mL), filtered and purified by reverse-phase HPLC to give the title compound as a yellowish solid. LR-MS (API-ES): calculated for C17H11ClN2O3 326.1, observed m/e 327.1 (M+H)+ (Rt 1.25 min).

Workup

  1. customThe solution was then evaporated to dryness in vacuo
  2. customto give brownish oil, which
  3. filtrationfiltered
  4. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-fcaeb791d57842cdb124abe7a667818e
Source dataset
uspto-grants-2013_10
Patent number
US08563746B2

Reaction notes

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