Sodium hydride → HCID 70114640, compound

HRID 324448Notes

Reaction equation

HRID 324448 reaction equation
O[C:2]1([C:18]2[C:19](=[O:25])[NH:20][C:21](=[O:24])[NH:22][CH:23]=2)[C:8]2[N:9]=[C:10]([CH3:12])[S:11][C:7]=2[CH2:6][CH2:5][C:4]2[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:3]1=2.[H-].[Na+].Cl.Cl[CH2:30][CH2:31][N:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>CN(C)C=O.C(O)(=O)C>[CH3:12][C:10]1[S:11][C:7]2[CH:6]=[CH:5][C:4]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:3]=3[CH:2]([C:18]3[C:19](=[O:25])[NH:20][C:21](=[O:24])[N:22]([CH2:30][CH2:31][N:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)[CH:23]=3)[C:8]=2[N:9]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 70112528HCID 70112528, compound

Product 1

HCID 70114640HCID 70114640, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

The product from example 18 step (ii) (1.44 g) was dissolved in dry N,N-dimethylformamide (20 ml) and treated cautiously with sodium hydride (60% dispersion by wt, 0.5 g) under nitrogen. After 10 min 1-(2-chloroethyl)pyrrolidine hydrochloride (0.8 g) was added and the whole heated at 50° C. for 16 h. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was collected, dried over magnesium sulphate and solvent evaporated under reduced pressure. Purification was by flash chromatography eluting with 9:1 dichloromethane/methanol. The product obtained was dissolved in acetic acid (10 ml) and heated at 100° C. for 2 h. The solvent was removed under reduced pressure. Purification was by flash chromatography eluting with dichloromethane/methanol mixtures to give the subtitle product as pale yellow foam.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customThe organic layer was collected
  3. dry with materialdried over magnesium sulphate and solvent
  4. customevaporated under reduced pressure
  5. customPurification
  6. washeluting with 9:1 dichloromethane/methanol
  7. customThe product obtained
  8. temperatureheated at 100° C. for 2 h
  9. customThe solvent was removed under reduced pressure
  10. customPurification
  11. washeluting with dichloromethane/methanol

Sources & evidence

ORD record
ord-ef06efa5b06343ba99cd196498e5dfe1
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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