Dimethylformamide → HCID 19842351, compound

HRID 1638356Notes

Reaction equation

HRID 1638356 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.O[N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2N=N1.[ClH:18].CN(C)CCCN=C=NCC.CN([CH:33]=[O:34])C>>[ClH:18].[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:33]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([NH2:9])[CH:12]=2)=[O:34])[CH2:4][CH2:3]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 19842351HCID 19842351, compound

Procedure

Dissolve 3.0 g of the product of Preparation 3, 1.3 g of N-methylpiperazine, 1.9 g of 1-hydroxybenzotriazole and 2.7 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 10 ml of DMF. Stir for 18 hrs. and then concentrate in vacuo. Dissolve the resultant residue in 100 ml of ethyl acetate, wash with 20 ml of 1N NaHCO3 solution, and 20 ml of saturated sodium chloride solution. Dry the organic layer over MgSO4, filter and concentrate in vacuo. Dissolve 1.68 g of this residue in 10 ml of HCl:dioxane and stir for 2 hrs. Concentrate in vacuo to obtain the title compound as a white solid, mass spec M+=219.

Workup

  1. dissolutionDissolve
  2. concentrationand then concentrate in vacuo
  3. dissolutionDissolve the resultant residue in 100 ml of ethyl acetate
  4. washwash with 20 ml of 1N NaHCO3 solution, and 20 ml of saturated sodium chloride solution
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. dissolutionDissolve 1.68 g of this residue in 10 ml of HCl
  9. stirringdioxane and stir for 2 hrs
  10. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-779c5b2163fc4ad0aea9947959f3972b
Source dataset
uspto-grants-1989_11
Patent number
US04879309

Reaction notes

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