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1,1'-Carbonyldiimidazole → 6-(1-Methanesulfonyl-1-methyl-ethyl)-8-[3-(3-methyl-[1,2,4]oxadiazol-5-yl)-phenyl]-quinoline

HRID 861012
Notes
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Reaction equation

HRID 861012 reaction equation
[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=3)[C:21]([OH:23])=O)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6])(=[O:4])=[O:3].C1N=CN(C(N2C=NC=C2)=O)C=1.O[NH:40][C:41](=[NH:43])[CH3:42]>CN(C=O)C.O>[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:26]=[CH:25][CH:24]=[C:20]([C:21]4[O:23][N:43]=[C:41]([CH3:42])[N:40]=4)[CH:19]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:6])[CH3:7])(=[O:4])=[O:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 218655663-{6-[1-Methyl-1-(methylsulfonyl)ethyl]quinolin-8-yl}benzoic acidHCID 178465666HCID 178465666, compound

Product 1

HCID 99787446-(1-Methanesulfonyl-1-methyl-ethyl)-8-[3-(3-methyl-[1,2,4]oxadiazol-5-yl)-phenyl]-quinoline

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

To a solution of-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-benzoic acid from Step 2 (1.0 eq.) in DMF (0.1M) was added CDI (2.0 eq.) and N-hydroxy-acetamidine (2.0 eq.). The mixture was stirred for 1 h at rt then 12 h at 120° C. The mixture was cooled, poured in water and extracted with EtOAc. The organic extract was washed with water (2×), brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 9:1 to 1:9 in 20 min) afforded the title compound as a white solid. 1H NMR (500 MHz, acetone-d6): δ 8.91 (dd, 1H), 8.52 (m, 3H), 8.38 (d, 1H), 8.25 (d, 1H), 8.04 (d, 1H), 7.78 (t, 1H), 7.64 (dd, 1H), 2.77 (s, 3H), 2.43 (s, 3H), 2.05 (s, 6H).

Workup

  1. custom12 h
  2. customat 120° C
  3. temperatureThe mixture was cooled
  4. extractionextracted with EtOAc
  5. extractionThe organic extract
  6. washwas washed with water (2×), brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a1d8c6aa7c8049c6a98f8061486932cf
Source dataset
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07153968B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes