1,1'-Carbonyldiimidazole → HCID 178455693, compound

HRID 505636Notes

Reaction equation

HRID 505636 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]([C:14]([NH:16][C@:17]2([C:22]([OH:24])=O)[CH2:19][C@H:18]2[CH:20]=[CH2:21])=[O:15])[C:11]2=[N:25][NH:26][CH:27]=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH:40]1([S:43]([NH2:46])(=[O:45])=[O:44])[CH2:42][CH2:41]1.C1CCN2C(=NCCC2)CC1>ClCCCl>[CH:40]1([S:43]([NH:46][C:22]([C@@:17]2([NH:16][C:14]([CH:12]3[CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:9][C:10]4=[CH:27][NH:26][N:25]=[C:11]34)=[O:15])[CH2:19][C@H:18]2[CH:20]=[CH2:21])=[O:24])(=[O:45])=[O:44])[CH2:42][CH2:41]1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15765418CyclopropanesulfonamideHCID 178455694HCID 178455694, compound

Product 1

HCID 178455693HCID 178455693, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of acid 8b (47.0 mg, 0.125 mmol) and CDI (22.3 mg, 0.150 mmol) in dry DCE (1.0 mL) was stirred at rt for 8 h. The cyclopropyl sulfonamide 9b (18.2 mg, 0.150 mmol) and DBU (22.8 mg, 0.150 mmol) were sequentially added and the mixture stirred at rt for 48 h. The solvent was evaporated and the residue diluted with EtOAc (2 mL). The mixture was washed sequentially with 0.5 M HCl (2×), deionized H2O and brine. The EtOAc solution was dried over MgSO4, filtered through a Celite plug capped with a layer of MgSO4 and concentrated. The crude product was purified via a SiO2 column (CH2Cl2, 25% EtOAc/hexanes then 50% EtOAc/hexanes) to give compound 104 as an ivory solid; 3:2 mixture of diastereomers, 27 mg, 45% (3:2 mixture of diastereomers), MS m/z 478.1 (APCI−, M−1).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue diluted with EtOAc (2 mL)
  3. washThe mixture was washed sequentially with 0.5 M HCl (2×)
  4. dry with materialThe EtOAc solution was dried over MgSO4
  5. filtrationfiltered through a Celite plug
  6. customcapped with a layer of MgSO4
  7. concentrationconcentrated
  8. customThe crude product was purified via a SiO2 column (CH2Cl2, 25% EtOAc/hexanes

Sources & evidence

ORD record
ord-14ee39a6ce9e4ab5a22412baba4d9102
Source dataset
uspto-grants-2010_08
Patent number
US07781474B2

Reaction notes

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