Hexane → HCID 22048483, compound

HRID 1830799Notes

Reaction equation

HRID 1830799 reaction equation
[Li]CCCC.CCCCCC.[S:12]1[CH:16]=[CH:15][N:14]=[CH:13]1.[Cl:17][C:18]1[CH:19]=[C:20]([C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([C:34]([C:36]4[N:40]([CH3:41])[CH:39]=[N:38][CH:37]=4)=[O:35])[CH:32]=3)[N:27]=[C:26]([O:42][CH3:43])[CH:25]=2)[CH:21]=[CH:22][CH:23]=1>C(OCC)C.C1COCC1>[Cl:17][C:18]1[CH:19]=[C:20]([C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([C:34]([C:36]4[N:40]([CH3:41])[CH:39]=[N:38][CH:37]=4)([C:13]4[S:12][CH:16]=[CH:15][N:14]=4)[OH:35])[CH:32]=3)[N:27]=[C:26]([O:42][CH3:43])[CH:25]=2)[CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 9256ThiazoleHCID 22048493HCID 22048493, compoundHCID 178418339Butyllithium

Product 1

HCID 22048483HCID 22048483, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

BuLi 1.6 M in hexane (0.0111 mol) was added dropwise at −70° C. under N2 flow to a mixture of thiazole (0.0111 mol) in diethyl ether (30 ml). The mixture was stirred at −70° C. for 1 hour. A mixture of intermediate (9) (0.0074 mol) in THF (30 ml) was added dropwise. The mixture was stirred at −70° C. for 1 hour, hydrolyzed and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue (4 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1; 15–40 μm). The pure fractions were collected and the solvent was evaporated, yielding 3.1 g (91.1%) of 4-(3-chlorophenyl)-2-methoxy-α-(1-methyl-1H-imidazol-5-yl)-α-(2-thiazolyl)-6-quinolinemethanol (intermediate 10).

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred at −70° C. for 1 hour
  3. extractionhydrolyzed and extracted with EtOAc
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated till dryness
  8. customThe residue (4 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1; 15–40 μm)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9f74733bdfe74b28949b67bc093e805b
Source dataset
uspto-grants-2006_06
Patent number
US07067531B2

Reaction notes

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