1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 135610070, compound

HRID 1271605Notes

Reaction equation

HRID 1271605 reaction equation
C([CH:3]([O:7][C:8]1[CH:12]=[C:11]([C:13](O)=O)[O:10][N:9]=1)[C:4]([OH:6])=[O:5])C.CCN=C=NCCCN(C)C.Cl.[CH2:28]([N:31]1[C:38]([NH2:39])=[C:37]([NH2:40])[C:35](=[O:36])[N:34]([CH2:41][CH2:42][CH3:43])[C:32]1=[O:33])[CH2:29][CH3:30]>CO>[CH2:41]([N:34]1[C:35](=[O:36])[C:37]2[NH:40][C:13]([C:11]3[O:10][N:9]=[C:8]([O:7][CH2:3][C:4]([OH:6])=[O:5])[CH:12]=3)=[N:39][C:38]=2[N:31]([CH2:28][CH2:29][CH3:30])[C:32]1=[O:33])[CH2:42][CH3:43]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedioneHCID 86590101HCID 86590101, compound

Product 1

HCID 135610070HCID 135610070, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of ethyl (5-carboxyisoxazol-3-yl)oxyacetic acid (0.5 mmol) and EDCl (0.5 mmol) in methanol (20 mL) was added a solution of 1,3-dipropyl-5,6-diaminouracil (0.5 mmol), dissolved in methanol (20 mL). The mixture was stirred at room temperature for two hours, the solvent was then removed in vacuo, water added, and the solid that formed was collected by filtration and washed with additional cold water. The intermediate amide was heated in 20 mL of 2.5 N NaOH at 70° C. for 30 minutes to afford the desired 2-[5-(1,3-dipropyl-xanthin-8-yl)-isoxazol-3-yl)oxyacetic acid.

Workup

  1. customthe solvent was then removed in vacuo, water
  2. additionadded
  3. customthe solid that formed
  4. filtrationwas collected by filtration
  5. washwashed with additional cold water
  6. temperatureThe intermediate amide was heated in 20 mL of 2.5 N NaOH at 70° C. for 30 minutes

Sources & evidence

ORD record
ord-3461e100a79343d39146170e1bb6e22a
Source dataset
uspto-grants-2007_04
Patent number
US07205403B2

Reaction notes

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