HCID 18672571, compound → HCID 21467209, compound

HRID 1939226Notes

Reaction equation

HRID 1939226 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)[N:8]([C:19](=[O:39])[C:20]1[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]4[N:36]=[C:35]([CH3:37])[O:34][N:33]=4)=[CH:28][C:27]=3[CH3:38])=[CH:22][CH:21]=1)[CH2:7][CH2:6]2.CC(C)([O-])C.[K+].CC1C=C(C2N=C(C)ON=2)C=CC=1C1C=CC(C(Cl)=O)=CC=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]1)[N:8]([C:19](=[O:39])[C:20]1[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]4[N:36]=[C:35]([CH3:37])[O:34][N:33]=4)=[CH:28][C:27]=3[CH3:38])=[CH:22][CH:21]=1)[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 18672571HCID 18672571, compoundHCID 23209440HCID 23209440, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21467209HCID 21467209, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of intermediate 2 (300 mg, 0.0012 mole) in dry THF (30 ml) under argon was treated with potassium t-butoxide (140 mg, 0.0012 mole) and kept at room temperature for 20 minutes. The resulting mixture was treated with a solution of 4-[2-methyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]benzoyl chloride (0.0014 mole) in dry THF (10 ml) and the mixture stirred at room temperature for 20h. The solution was concentrated in vacuo and the residue treated with 10% Na2CO3 solution (20 ml) and extracted with dichloromethane (2×40 ml). The combined extract was dried (Na2SO4), concentrated in vacuo and the residue chromatographed on silica gel eluting with 0-3% methanol/dichloromethane. The tide compound was obtained as a yellow solid on crystallisation from ethyl acetate/60-80 petrol (220 mg, 35%) mp 175°-177° C.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. additionthe residue treated with 10% Na2CO3 solution (20 ml)
  3. extractionextracted with dichloromethane (2×40 ml)
  4. extractionThe combined extract
  5. dry with materialwas dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customthe residue chromatographed on silica gel eluting with 0-3% methanol/dichloromethane
  8. customThe tide compound was obtained as a yellow solid on crystallisation from ethyl acetate/60-80 petrol (220 mg, 35%) mp 175°-177° C.

Sources & evidence

ORD record
ord-dfb880a513ed484698bd673938f5defe
Source dataset
uspto-grants-1997_12
Patent number
US05696122

Reaction notes

Loading…