Sodium hydride → HCID 10311074, compound

HRID 857288Notes

Reaction equation

HRID 857288 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([C:14]3[CH:15]=[C:16]([CH:29]=[CH:30][CH:31]=3)[CH2:17][NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([CH3:3])[CH3:2].[H-].[Na+].[CH:34]1([CH2:37]Br)[CH2:36][CH2:35]1>CN(C=O)C>[CH:34]1([CH2:37][N:18]([CH2:17][C:16]2[CH:29]=[CH:30][CH:31]=[C:14]([C:12]3[CH:13]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=[C:6]4[C:11]=3[N:10]=[CH:9][CH:8]=[CH:7]4)[CH:15]=2)[C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 21865649HCID 21865649, compound

Product 1

HCID 10311074HCID 10311074, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To solution of the previous amine from step 2 (1.1 eq) in DMF (0.12M) was added NaH (60% dispersion in oil; 3.0 eq). The mixture was stirred for 15 min, then cyclopropylmethyl bromide was added (1.2 eq). The final mixture was stirred for 12 h, quenched with AcOH, poured in water and extracted with Et2O. The combined organic extracts were washed with water (2×), brine, dried over Na2 SO4, filtered and concentrated. Flash chromatography (Tol:Ace; 9:1) afforded the title compound as a foam.

Workup

  1. customquenched with AcOH
  2. additionpoured in water
  3. extractionextracted with Et2O
  4. washThe combined organic extracts were washed with water (2×), brine
  5. customdried over Na2 SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-95ebdc18cb8c43f7841b00ea91c403bf
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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