Dimethylamine → HCID 58124847, compound

HRID 1971746Notes

Reaction equation

HRID 1971746 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:7]([O:35][CH3:36])=[CH:8][C:9]2[CH2:10][CH2:11][N:12]3[C:18]4[C:19](=[O:29])[N:20]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:21][CH2:22][CH2:23][CH2:24][C:17]=4[C:16]([C:30]4[S:31][CH:32]=[CH:33][CH:34]=4)=[C:13]3[C:14]=2[CH:15]=1)=[O:4].[CH2:37]([N:39](CC)[CH2:40]C)C.CNC>CN(C=O)C.C1COCC1>[CH3:37][N:39]([CH3:40])[CH2:2][C:3]([NH:5][C:6]1[C:7]([O:35][CH3:36])=[CH:8][C:9]2[CH2:10][CH2:11][N:12]3[C:18]4[C:19](=[O:29])[N:20]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:21][CH2:22][CH2:23][CH2:24][C:17]=4[C:16]([C:30]4[S:31][CH:32]=[CH:33][CH:34]=4)=[C:13]3[C:14]=2[CH:15]=1)=[O:4]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 8471TriethylamineHCID 58124891HCID 58124891, compound

Product 1

HCID 58124847HCID 58124847, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 392 mg of 22a in 3 ml of DMF was treated with 0.5 ml of triethylamine and 2 ml of a 2M solution of dimethylamine in THF. The reaction mixture was sealed and heated at an oil bath at 60° C. for 40 min. The clear solution was poured onto water and extracted with ethyl acetate. The extract was washed, dried and concentrated and the residue was purified by chromatography over silicagel, using a gradient of CH2Cl2-methanol. The material thus isolated was triturated with diethylether, to provide 438 mg of crystalline material.

Workup

  1. customThe reaction mixture was sealed
  2. additionThe clear solution was poured onto water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was purified by chromatography over silicagel
  8. customThe material thus isolated
  9. customwas triturated with diethylether

Sources & evidence

ORD record
ord-67fc9baf38dd4de591a7d8e20958fc17
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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