1,1'-Carbonyldiimidazole → HCID 73231858, compound

HRID 406403Notes

Reaction equation

HRID 406403 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([O:14][CH:15]2[CH2:32][CH:31]3[N:17]([C:18](=[O:37])[O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH:25][CH:26]4[C:28]([C:34](O)=[O:35])([NH:29][C:30]3=[O:33])[CH2:27]4)[CH2:16]2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:50]1([S:53]([NH2:56])(=[O:55])=[O:54])[CH2:52][CH2:51]1.C1CCN2C(=NCCC2)CC1>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([O:14][CH:15]2[CH2:32][CH:31]3[N:17]([C:18](=[O:37])[O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH:25][CH:26]4[C:28]([C:34]([NH:56][S:53]([CH:50]5[CH2:52][CH2:51]5)(=[O:55])=[O:54])=[O:35])([NH:29][C:30]3=[O:33])[CH2:27]4)[CH2:16]2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15765418CyclopropanesulfonamideHCID 73231857HCID 73231857, compound

Product 1

HCID 73231858HCID 73231858, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 16 (120 mg, 0.23 mmol) and carbonyldiimidazole (44 mg, 0.27 mmol) in dry THF (25 mL) was refluxed for 3 h under nitrogen. Optionally, the azalactone derivative, if desired, can be isolated. Then, the reaction mixture was cooled to room temperature and cyclopropylsulfonamide (33 mg, 0.27 mmol) and DBU (52 mg, 0.34 mmol) were added. The reaction mixture was heated at 50° C. for 24 h, then cooled down at room temperature and partitioned between water and CH2Cl2. The organic layers were dried (MgSO4), filtered, and the solvent was evaporated. The crude material was purified by column chromatography on silica gel (CH2Cl2/EtOAc, 95:05) to give a solid which was successively triturated in water, filtered, dried, triturated in ether and dried again under high vacuum to give 23 mg (16%) of the title product 17 as a white powder: m/z=530 (M+H)+; 1H NMR (CDCl3): 8.10 (d, J=9.3 Hz, 1H), 7.50 (s, 1H); 7.39 (s, 1H); 7.25 (dd, J=9.3 Hz, 2.5 Hz, 1H); 7.39-7.30 (bs, 1H); 5.90-5.83 (bs, 1H); 5.71 (dd, J=8.0 Hz, 17.9 Hz, 1H); 5.18 (t, J=10.1 Hz, 1H), 4.79 (dd, J=7.3 Hz, 9.0 Hz, 1H), 4.1 (s, 3H), 4.09-3.97 (m, 1H), 3.81-3.66 (m, 2H), 3.62 (d, J=11.6 Hz, 1H), 3.19-3.05 (m, 1H); 2.59-2.22 (m, 4H); 2.01-1.90 (m, 1H), 1.89 (dd, J=5.8 Hz, 8.6 Hz, 1H), 1.70 (dd, J=6.1 Hz, 9.8 Hz, 1H), 1.67-1.58 (m, 2H), 1.75-0.76 (m, 7H).

Workup

  1. customcan be isolated
  2. temperatureThe reaction mixture was heated at 50° C. for 24 h
  3. temperaturecooled down at room temperature
  4. custompartitioned between water and CH2Cl2
  5. dry with materialThe organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe crude material was purified by column chromatography on silica gel (CH2Cl2/EtOAc, 95:05)
  9. customto give a solid which
  10. customwas successively triturated in water
  11. filtrationfiltered
  12. customdried
  13. customtriturated in ether
  14. customdried again under high vacuum

Sources & evidence

ORD record
ord-65498a8a62f2445f9d252e6a994be4d7
Source dataset
uspto-grants-2014_06
Patent number
US08754105B2

Reaction notes

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