1,1'-Carbonyldiimidazole → HCID 67319632, compound

HRID 1669553Notes

Reaction equation

HRID 1669553 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[C:10]([O:12][CH:13]1[CH2:31][CH:30]2[N:15]([C:16](=[O:36])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH:24][CH:25]3[C:27]([C:33](O)=[O:34])([NH:28][C:29]2=[O:32])[CH2:26]3)[CH2:14]1)=[O:11].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH:49]1([S:52]([NH2:55])(=[O:54])=[O:53])[CH2:51][CH2:50]1.C1CCN2C(=NCCC2)CC1>C1COCC1>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][N:2]1[C:10]([O:12][CH:13]1[CH2:31][CH:30]2[N:15]([C:16](=[O:36])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH:24][CH:25]3[C:27]([C:33]([NH:55][S:52]([CH:49]4[CH2:51][CH2:50]4)(=[O:54])=[O:53])=[O:34])([NH:28][C:29]2=[O:32])[CH2:26]3)[CH2:14]1)=[O:11]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15765418CyclopropanesulfonamideHCID 67319780HCID 67319780, compound

Product 1

HCID 67319632HCID 67319632, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of carboxylic acid 18 (30 mg, 0.06 mmole) and CDI (20 mg, 2 eq) in dry THF (3 mL) was stirred at reflux for 2 h30 under nitrogen. Optionally, the azalactone derivative, if desired, can be isolated. Then, the reaction mixture was cooled at room temperature and cyclopropylsulfonamide (15 mg, 2 eq) and DBU (18 mg, 2 eq) were added. The reaction mixture was stirred at 50° C. until completion as indicated by LC-MS. The RM was then concentrated, redissolved in DCM and extracted with HCl 1M then brine, dried and concentrated. Purification by flash chromatography on silica gel afforded the desired product 19. m/z=599 (M+H+).

Workup

  1. temperatureat reflux for 2 h30 under nitrogen
  2. customcan be isolated
  3. stirringThe reaction mixture was stirred at 50° C. until completion
  4. concentrationThe RM was then concentrated
  5. dissolutionredissolved in DCM
  6. extractionextracted with HCl 1M
  7. dry with materialbrine, dried
  8. concentrationconcentrated
  9. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-cc63da3cf88f4d02aeb2432eacfa15a5
Source dataset
uspto-grants-2011_08
Patent number
US07989471B2

Reaction notes

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