1,1'-Carbonyldiimidazole → HCID 86649981, compound

HRID 1892472Notes

Reaction equation

HRID 1892472 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:12]=[C:13]([NH:16][C:17](=[O:19])[CH3:18])[S:14][CH:15]=2)=[CH:5][CH:4]=1.[C:20]([N:27]1C=CN=C1)(N1C=CN=C1)=[O:21].[C:32]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])(=[O:35])[NH:33]N>O1CCCC1>[NH:27]([C:20]([O:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:12]=[C:13]([NH:16][C:17](=[O:19])[CH3:18])[S:14][CH:15]=2)=[CH:5][CH:4]=1)=[O:21])[NH:33][C:32]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 70091tert-Butyl carbazate4×HCID 21914951HCID 21914951, compound

Product 1

HCID 86649981HCID 86649981, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N-(4-{2-[4-(hydroxymethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (161.5 mg, 0.584 mmol) in anhydrous tetrahydrofuran (2.4 ml) was added 1,1′-carbonyldiimidazole (142.1 mg, 0.876 mmol), and the mixture was stirred at room temperature for 1.5 hr. tert-Butyl carbazate (115.9 mg, 0.877 mmol) was added, and the mixture was stirred for 16 hr. tert-Butyl carbazate (77.3 mg, 0.584 mmol) was added, and the mixture was stirred for 4 hr. tert-Butyl carbazate (77.3 mg, 0.584 mmol) was added again, and the mixture was stirred for 2 hr. tert-Butyl carbazate (115.9 mg, 0.877 mmol) was added again, and the mixture was stirred for 4 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 10 g, ethyl acetate:hexane=5:5→6:4→7:3). The residue was further purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. DM2035 5 g, ethyl acetate:hexane=5:5→1:0) to give 4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}benzyl tert-butyl hydrazine-1,2-dicarboxylate (207.0 mg, 0.476 mmol, yield 81.6%) as a white solid.

Workup

  1. stirringthe mixture was stirred for 16 hr
  2. stirringthe mixture was stirred for 4 hr
  3. stirringthe mixture was stirred for 2 hr
  4. stirringthe mixture was stirred for 4 hr
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 10 g, ethyl acetate:hexane=5:5→6:4→7:3)
  7. customThe residue was further purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. DM2035 5 g, ethyl acetate:hexane=5:5→1:0)

Sources & evidence

ORD record
ord-29d72986375f445fad5f224d7794d4bd
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

Loading…