1,1'-Carbonyldiimidazole → HCID 58963166, compound

HRID 917530Notes

Reaction equation

HRID 917530 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:14]2[CH:15]=[C:16]([CH2:24][CH3:25])[C:17]3[O:21][CH:20]=[C:19]([CH3:22])[C:18]=3[CH:23]=2)[C:11](O)=[O:12])=[CH:5][CH:4]=1)#[N:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[S:38]([NH2:42])([NH2:41])(=[O:40])=[O:39].CCCCCCC=CCCC>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH:10]([C:14]2[CH:15]=[C:16]([CH2:24][CH3:25])[C:17]3[O:21][CH:20]=[C:19]([CH3:22])[C:18]=3[CH:23]=2)[C:11]([NH:41][S:38]([NH2:42])(=[O:40])=[O:39])=[O:12])=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 82267SulfamideHCID 136496Undec-4-eneHCID 58963169HCID 58963169, compound

Product 1

HCID 58963166HCID 58963166, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Cyanophenylamino)-2-(7-ethyl-3-methylbenzofuran-5-yl)acetic acid 6 (5.45 g, 16.4 mmoles), carbonyldiimidazole (CDI, 5.28 g 32.6 mmoles) were combined under a nitrogen atmosphere and THF (50 ml) added. The reaction was stirred for 1 h. Sulfamide (4.7 g, 49 mmoles) was added to the reaction followed by drop wise addition of 1,8-diazabiocyclo[5.4.0]undec-7-ene (DBU, 7.3 ml, 49 mmoles). The reaction was then stirred an additional 2 hours at room temperature and the solvent removed in vacuo. The residue was taken up in ethyl acetate (ca. 150 ml) and washed with aqueous 2 N HCl. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to a yellow foam. The crude product was then purified on a silica flash column eluted with 40% ethyl acetate/60% hexane to provide 2-(4-cyanophenylamino)-2-(7-ethyl-3-methylbenzofuran-5-yl)acetylsulfamide 7 (4.7 g).

Workup

  1. stirringThe reaction was then stirred an additional 2 hours at room temperature
  2. customthe solvent removed in vacuo
  3. washwashed with aqueous 2 N HCl
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow foam
  7. customThe crude product was then purified on a silica flash column
  8. washeluted with 40% ethyl acetate/60% hexane

Sources & evidence

ORD record
ord-ee7ccecb93da42569a84169f38cda967
Source dataset
uspto-grants-2007_09
Patent number
US07273886B2

Reaction notes

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