1,1'-Carbonyldiimidazole → HCID 69231263, compound

HRID 406607Notes

Reaction equation

HRID 406607 reaction equation
[C:1]1([C:7]2[N:8]=[N:9][N:10]([CH:12]3[CH2:29][CH:28]4[CH:14]([C:15](=[O:35])[N:16]([CH3:34])[CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH:22][CH:23]5[C:25]([C:31]([OH:33])=O)([NH:26][C:27]4=[O:30])[CH2:24]5)[CH2:13]3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH:48]1([S:51]([NH2:54])(=[O:53])=[O:52])[CH2:50][CH2:49]1.C1CCN2C(=NCCC2)CC1>C1COCC1>[C:1]1([C:7]2[N:8]=[N:9][N:10]([CH:12]3[CH2:29][CH:28]4[CH:14]([C:15](=[O:35])[N:16]([CH3:34])[CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH:22][CH:23]5[C:25]([C:31]([NH:54][S:51]([CH:48]6[CH2:50][CH2:49]6)(=[O:53])=[O:52])=[O:33])([NH:26][C:27]4=[O:30])[CH2:24]5)[CH2:13]3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15765418Cyclopropanesulfonamide2×HCID 69233646HCID 69233646, compound

Product 1

HCID 69231263HCID 69231263, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 9 (50 mg, 0.104 mmol) and CDI (68 mg, 0.418 mmol) in dry THF (5 mL) was heated at reflux for 2 h under nitrogen. The reaction mixture was cooled to room temperature and cyclopropylsulfonamide (101 mg, 0.836 mmol) was added. Then, DBU (73 mg, 0.481 mmol) was added and the reaction mixture was stirred at room temperature for 1 h, and then heated at 55° C. for 24 h. Solvent was evaporated, and the residue partitioned between AcOEt and acidic water (pH=3). The crude material was purified by column chromatography (AcOEt/CH2Cl2/Petroleum ether, 1:1:1). The residue was crystallized in Et2O, filtered to give the target compound contaminated with the cyclopropylsulfonamide. This material was triturated in 1.5 mL of water, filtered, washed with water and dried overnight in the high vacuum pump to give 28 mg (46%) of the target compound as a white powder: m/z=582 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h under nitrogen
  3. temperatureheated at 55° C. for 24 h
  4. customSolvent was evaporated
  5. customthe residue partitioned between AcOEt and acidic water (pH=3)
  6. customThe crude material was purified by column chromatography (AcOEt/CH2Cl2/Petroleum ether, 1:1:1)
  7. customThe residue was crystallized in Et2O
  8. filtrationfiltered
  9. customto give the target compound
  10. customThis material was triturated in 1.5 mL of water
  11. filtrationfiltered
  12. washwashed with water
  13. customdried overnight in the high vacuum pump

Sources & evidence

ORD record
ord-d736a49d1b754cb8b25b1c8f12815551
Source dataset
uspto-grants-2014_06
Patent number
US08754116B2

Reaction notes

Loading…