Acetic Acid → HCID 53247540, compound

HRID 1172987Notes

Reaction equation

HRID 1172987 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([NH2:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].C(O)(=O)C.[C:31]([O:35][CH3:36])(=[O:34])[CH:32]=[CH2:33]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([NH:26][CH2:33][CH2:32][C:31]([O:35][CH3:36])=[O:34])([CH3:24])[CH3:25])=[CH:19][CH:18]=3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7294Methyl Acrylate2×HCID 53247538HCID 53247538, compound

Product 1

HCID 53247540HCID 53247540, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

2-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl) phenyl)propan-2-amine, acetic acid (132 mg, 0.306 mmol) was added to a 5 mL microwave vial equipped with a stirring bar. Methyl acrylate (52.6 mg, 0.611 mmol), and MeOH (3.0 mL) were added, the vial capped, and the reaction heated to 120° C. for 90 min under microwave irradiation (Biotage Optimizer, 300 W). After 90 min another aliquot of methyl acrylate (52.6 mg, 0.611 mmol) was added and the reaction submitted for another 60 min at 120° C. Reaction was cooled and the solvent removed under reduced pressure. Crude material was purified by RP-HPLC (A=50 mM ammonium acetate, B=acetonitrile; 30-70% B over 30.0 min (21.0 mL/min flow rate); 21.2×250 mm Thermo Hyperprep C18 column, 8 μm particles) to give methyl 3-(2-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)propan-2-ylamino)propanoate (83.5 mg; 59.7%). LCMS (Table 1, Method f) Rt=2.78 min, m/z=458.29 (M+H)+,

Workup

  1. customvial equipped with a stirring bar
  2. customReaction
  3. temperaturewas cooled
  4. customthe solvent removed under reduced pressure
  5. customCrude material was purified by RP-HPLC (A=50 mM ammonium acetate, B=acetonitrile
  6. wait30-70% B over 30.0 min (21.0 mL/min flow rate)

Sources & evidence

ORD record
ord-222ff1f2bdf44a6389688ee431021f49
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

Loading…