Water → HCID 53713215, compound

HRID 442863Notes

Reaction equation

HRID 442863 reaction equation
Cl.C[N:3](C)[CH2:4][CH2:5][CH2:6]N=C=NCC.[CH3:13][N:14]([CH3:42])[CH2:15][CH2:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:18]1[C:39](O)=[O:40].C(N)CC.O>C(Cl)Cl>[CH2:4]([NH:3][C:39]([C:18]1[N:17]([CH2:16][CH2:15][N:14]([CH3:13])[CH3:42])[C:25]2[C:20]([C:19]=1[CH:26]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:40])[CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 7852PropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22440043HCID 22440043, compound

Product 1

HCID 53713215HCID 53713215, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.45 g, 7.53 mmol) was added to a solution of Compound 93 (1.5 g, 3.76 mmol) obtained in Example 93 and propylamine (0.47 ml, 5.65 mmol) in 50 ml of methylene chloride, followed by stirring at room temperature for 4.5 hours. Water was added to the reaction solution followed by extraction with chloroform. The resulting organic layer was washed successively with water and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to give a crude product. The obtained crude product was purified with silica gel column chromatography (chloroform/methanol=40/1) followed by recrystallization from diisopropyl ether to give 0.98 g (yield: 59%) of the title compound.

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe resulting organic layer was washed successively with water
  3. dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto give a crude product
  6. customThe obtained crude product
  7. customwas purified with silica gel column chromatography (chloroform/methanol=40/1)
  8. customfollowed by recrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-58b8e97d422b488984902f3c23b43fa9
Source dataset
uspto-grants-1999_04
Patent number
US05891902

Reaction notes

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