Dimethylamine → HCID 22049710, compound

HRID 1830870Notes

Reaction equation

HRID 1830870 reaction equation
C[C:2]1[C:3]([C:11]2[S:12][CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[N:15]=2)=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=O.C[CH2:24][N:25]=[C:26]=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CNC>CO.CN(C)C=O>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:14]2[N:15]=[C:11]([C:3]3[CH:2]=[N:10][CH:9]=[CH:8][C:4]=3[C:5]([N:25]([CH3:26])[CH3:24])=[O:7])[S:12][CH:13]=2)=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 22049678HCID 22049678, compound

Product 1

HCID 22049710HCID 22049710, compoundYield 69.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

The compound (141) (170 mg, 0.5 mmol) was dissolved in methanol (10 ml)-1N NaOH aq. (10 ml) and the mixture was stirred at 40° C. for one hr. The pH of the reaction mixture was adjusted to around 6, and the precipitated solid was collected by filtration, which was dried in vacuo and dissolved in dimethylformamide (3 ml) together with WSC (117 mg, 0.6 mmol), HOBt (85 mg, 0.6 mmol) and dimethylamine (27 mg, 0.6 mmol). The mixture was stirred at 30° C. for 2 hrs. The reaction mixture was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate. The aqueous layer was extracted with ethyl acetate, and the organic layers were combined and dried (MgSO4). The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as white crystals (120 mg, 35%).

Workup

  1. filtrationthe precipitated solid was collected by filtration, which
  2. customwas dried in vacuo
  3. stirringThe mixture was stirred at 30° C. for 2 hrs
  4. customThe reaction mixture was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4c33d2a4517d4963ac194c7546349c74
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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