1,1'-Carbonyldiimidazole → HCID 86650046, compound

HRID 1892541Notes

Reaction equation

HRID 1892541 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[SH:13][CH2:14][C:15]1[S:19][C:18]([CH2:20][CH2:21][C:22]2[N:23]=[C:24]([NH:27][C:28](=[O:30])[CH3:29])[S:25][CH:26]=2)=[CH:17][CH:16]=1.[C:31]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])(=[O:34])[NH:32][NH2:33]>O1CCCC1>[C:28]([NH:27][C:24]1[S:25][CH:26]=[C:22]([CH2:21][CH2:20][C:18]2[S:19][C:15]([CH2:14][S:13][C:1]([NH:33][NH:32][C:31]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:2])=[CH:16][CH:17]=2)[N:23]=1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 70091tert-Butyl carbazateHCID 86650047HCID 86650047, compound

Product 1

HCID 86650046HCID 86650046, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1,1′-carbonyldiimidazole (326.0 mg, 2.010 mmol) in anhydrous tetrahydrofuran (8 ml), a solution of N-(4-{2-[5-(sulfanylmethyl)thiophen-2-yl]ethyl}-1,3-thiazol-2-yl)acetamide (400.0 mg, 1.340 mmol) in anhydrous tetrahydrofuran (10 ml) was added dropwise at 0° C. The mixture was stirred at 0° C. for 15 min and at room temperature for 1 hr. tert-Butyl carbazate (351.4 mg, 4.021 mmol) was added, and the mixture was stirred at room temperature for 16 hr. The mixture was concentrated, and residue was added water (40 ml) and extracted 3 times with ethyl acetate. The combined organic layer was washed with ice-cooled 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 100 g, ethyl acetate:hexane=1:1) to give tert-butyl 2-({[(5-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}thiophen-2-yl)methyl]sulfanyl}carbonyl)hydrazinecarboxylate (316.7 mg, 0.694 mmol, yield 51.8%) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hr
  2. concentrationThe mixture was concentrated
  3. additionresidue was added water (40 ml)
  4. extractionextracted 3 times with ethyl acetate
  5. washThe combined organic layer was washed with ice-
  6. temperaturecooled 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 100 g, ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-6c664c7107d94cfaacd3af97c134f5ca
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

Loading…