Sodium hydride → HCID 86588155, compound

HRID 1828560Notes

Reaction equation

HRID 1828560 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([CH2:9]O)[S:7][CH:8]=1)([CH3:3])[CH3:2].C1OCCOCCOCCOCCOCCOC1.[H-].[Na+].[CH:31]1([N:34]2[C:43]3[C:38](=[CH:39][C:40]([F:45])=[C:41](F)[CH:42]=3)[C:37](=[O:46])[C:36](/[CH:47]=[CH:48]/[C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[CH:35]2)[CH2:33][CH2:32]1.[Cl-].[NH4+]>CN(C)C=O>[CH:31]1([N:34]2[C:43]3[C:38](=[CH:39][C:40]([F:45])=[C:41]([CH2:9][C:6]4[S:7][CH:8]=[C:4]([CH:1]([CH3:2])[CH3:3])[N:5]=4)[CH:42]=3)[C:37](=[O:46])[C:36](/[CH:47]=[CH:48]/[C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[CH:35]2)[CH2:33][CH2:32]1

Participants

7

Reactant 5

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2855718-Crown-6HCID 10678505(4-Isopropylthiazol-2-yl)methanolHCID 86588156HCID 86588156, compound

Product 1

HCID 86588155HCID 86588155, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(4-Isopropyl-1,3-thiazol-2-yl)methanol (19.5 mg, 0.124 mmol) was dissolved in dimethylformamide (1 ml), added with 18-crown-6 (35.8 mg, 0.135 mmol) and sodium hydride (95%, 3.4 mg, 0.135 mmol), and stirred for 15 minutes under argon atmosphere. The reaction mixture was added with a solution of tert-butyl (E)-3-(1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydro-3-quinolyl)-2-propenoate (39.2 mg, 0.124 mmol) in dimethylformamide (1 ml) and stirred at room temperature for 3 hours. Then, the reaction mixture was added with aqueous ammonium chloride and extracted with chloroform. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative TLC (chloroform:methanol=100:1) to obtain the title compound (44.7 mg, 82%).

Workup

  1. stirringstirred at room temperature for 3 hours
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by preparative TLC (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-411874e5ec6d4826aba57da0c0bc4039
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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