Hydrochloric Acid → HCID 69112541, compound

HRID 900245Notes

Reaction equation

HRID 900245 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:10]([CH2:11][C:12]2[CH:16]=[C:15]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)[O:14][N:13]=2)[C:9]([C:23]([O:25]C(C)(C)C)=[O:24])=[CH:8][N:7]=1)=[O:5].Cl>CC(O)C>[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:10]([CH2:11][C:12]2[CH:16]=[C:15]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)[O:14][N:13]=2)[C:9]([C:23]([OH:25])=[O:24])=[CH:8][N:7]=1)=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69112445HCID 69112445, compound

Product 1

HCID 69112541HCID 69112541, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 24 mg of 3-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-3H-imidazole-2,4-dicarboxylic acid 4-tert-butyl ester 2-ethyl ester was added a 5 M solution of HCl in 2-propanol (2 mL). The mixture was stirred for 24 h at RT, concentrated in vacuo and the residue was purified by preparative HPLC (C18 reverse phase column, elution with a H2O/MeCN gradient with 0.1% TFA). The fractions containing the product were evaporated to provide 14 mg of the title compound as a pale yellow solid. Yield: 14 mg; MS (ESI+): m/e=381, chloro pattern.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was purified by preparative HPLC (
  3. washC18 reverse phase column, elution with a H2O/MeCN gradient with 0.1% TFA)
  4. additionThe fractions containing the product
  5. customwere evaporated

Sources & evidence

ORD record
ord-b6a6ef51748044208e8d9a57a3ca3e7f
Source dataset
uspto-grants-2008_04
Patent number
US07358268B2

Reaction notes

Loading…