1,1'-Carbonyldiimidazole → HCID 69233658, compound

HRID 406606Notes

Reaction equation

HRID 406606 reaction equation
[C:1]1([C:7]2[N:8]=[N:9][N:10]([CH:12]3[CH2:29][CH:28]4[N: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](O)=[O:32])([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[N: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:32])([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

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15765418Cyclopropanesulfonamide2×HCID 69233834HCID 69233834, compound

Product 1

HCID 69233658HCID 69233658, compound

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) is heated at reflux for 2 h under nitrogen. The reaction mixture is cooled to room temperature and cyclopropylsulfonamide (101 mg, 0.836 mmol) is added. Then, DBU (73 mg, 0.481 mmol) is added and the reaction mixture is stirred at room temperature for 1 h, and then heated at 55° C. for 24 h. Solvent is evaporated, and the residue partitioned between AcOEt and acidic water (pH=3). The crude material is purified by column chromatography (AcOEt/CH2Cl2/Petroleum ether, 1:1:1). The residue is crystallized in Et2O, filtered to give the target compound contaminated with the cyclopropylsulfonamide. This material is triturated in 1.5 mL of water, filtered, washed with water and dried overnight in the high vacuum pump to give the target compound.

Workup

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

Sources & evidence

ORD record
ord-2c688216ee0a4cda849bb685c39e1ed9
Source dataset
uspto-grants-2014_06
Patent number
US08754116B2

Reaction notes

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