Sodium hydride → HCID 67397624, compound

HRID 1426754Notes

Reaction equation

HRID 1426754 reaction equation
[H-].[Na+].C1OCCOCCOCCOCCOC1.[F:18][C:19]1[C:24]([C:25]2[NH:29][CH:28]=[C:27]([CH2:30][N:31]([CH3:39])[C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH:26]=2)=[CH:23][CH:22]=[CH:21][N:20]=1.[S:40]1[CH:44]=[CH:43][N:42]=[C:41]1[S:45](Cl)(=[O:47])=[O:46]>O1CCCC1.O>[F:18][C:19]1[C:24]([C:25]2[N:29]([S:45]([C:41]3[S:40][CH:44]=[CH:43][N:42]=3)(=[O:47])=[O:46])[CH:28]=[C:27]([CH2:30][N:31]([CH3:39])[C:32](=[O:38])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[CH:26]=2)=[CH:23][CH:22]=[CH:21][N:20]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 115792352-Thiazolesulfonyl chlorideHCID 67396538HCID 67396538, compound

Product 1

HCID 67397624HCID 67397624, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (60% in oil, 31 mg) in tetrahydrofuran (4 mL) were added dropwise 15-crown-5 (0.16 mL), a solution of tert-butyl {[5-(2-fluoropyridin-3-yl)-1H-pyrrol-3-yl]methyl}methylcarbamate (183 mg) in tetrahydrofuran (1 mL) and 1,3-thiazole-2-sulfonyl chloride (160 mg) under ice-cooling, and the mixture was stirred for 0.5 hr. The reaction mixture was diluted with water, and extracted with ethyl acetate. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→ethyl acetate) to give the title compound as a pale-yellow oil (yield 168 mg, 62%).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe separated aqueous layer was extracted again with ethyl acetate
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→ethyl acetate)

Sources & evidence

ORD record
ord-e65ce1052c2341e4b38d542da14d4b7d
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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