Diisopropylamine → HCID 86755484, compound

HRID 1421913Notes

Reaction equation

HRID 1421913 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([CH2:32][C:33]2[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=2)[C:8](=[O:9])[N:7]([CH2:10][CH:11]2[CH2:16][CH:15]3[CH2:17][CH:13]([C:14]3([CH3:19])[CH3:18])[CH:12]2[CH3:20])[C:6](=[CH:21][C:22]([C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=2)=[O:23])[NH:5]1.C(NC(C)C)(C)C.[CH3:46][S:47](Cl)(=[O:49])=[O:48]>C(Cl)Cl>[C:28]([C:27]1[CH:26]=[CH:25][C:24]([C:22](=[O:23])[CH:21]=[C:6]2[NH:5][C:4]([CH2:3][CH2:2][O:1][S:47]([CH3:46])(=[O:49])=[O:48])([CH2:32][C:33]3[CH:34]=[CH:35][N:36]=[CH:37][CH:38]=3)[C:8](=[O:9])[N:7]2[CH2:10][CH:11]2[CH2:16][CH:15]3[CH2:17][CH:13]([C:14]3([CH3:18])[CH3:19])[CH:12]2[CH3:20])=[CH:31][CH:30]=1)#[N:29]

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 31297Methanesulfonyl chlorideHCID 69943700HCID 69943700, compound

Product 1

HCID 86755484HCID 86755484, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-{[4-(2-Hydroxy-ethyl)-5-oxo-4-pyridin-4-ylmethyl-1-((+)-(2,6,6-trimethyl-bicyclo[3.1.1]hept-3-ylmethyl))-imidazolidin-2-ylidene]-acetyl}-benzonitrile (1.76 g, 3.44 mMol) and diisopropylamine (0.90 mL, 5.16 mMol) were dissolved in CH2Cl2 (20 mL) under an atmosphere of dry N2. To this solution was added methanesulfonyl chloride (0.41 mL, 5.16 mMol) and the mixture was stirred at ambient temperature for 20 minutes. The mixture was concentrated under vacuum and was partitioned between Et2O-EtOAc (50:50) and water. The organic layer was washed succesively with saturated aquoeus NaHCO3 solution, brine and then dried over MgSO4, filtered and concentrated under vacuum to give the titled compound as an oil as a 1:1 mixture of diastereomers.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customwas partitioned between Et2O-EtOAc (50:50) and water
  3. washThe organic layer was washed succesively with saturated aquoeus NaHCO3 solution, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-596e6a1208794c1d8f748ba1a2c08467
Source dataset
uspto-grants-2000_06
Patent number
US06080769

Reaction notes

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