HCID 21923071, compound → HCID 178478851, compound

HRID 1272661Notes

Reaction equation

HRID 1272661 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH2:8])[CH2:4][CH2:3]1.[Cl:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[C:12]([NH:24][C:25]2[CH:33]=[CH:32][C:28]([C:29]([NH2:31])=[O:30])=[CH:27][CH:26]=2)[N:11]=1>O>[ClH:9].[ClH:9].[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:10]2[N:18]=[C:17]3[C:13]([N:14]=[CH:15][N:16]3[CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)=[C:12]([NH:24][C:25]3[CH:26]=[CH:27][C:28]([C:29]([NH2:31])=[O:30])=[CH:32][CH:33]=3)[N:11]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 21923071HCID 21923071, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178478851HCID 178478851, compoundYield 116.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

The operation is carried out as in Stage 2 of Example 6 and 800 mg of trans-1,4-diaminocyclohexane is introduced at ambient temperature under agitation then the reaction medium is heated at approximately 150° C. until melting and 249 mg of the product obtained in Stage 1 above is added, the reaction medium is left under agitation for 4 hours 30 minutes then left to return to ambient temperature. Then 10 ml of water is added, followed by extracting with 10 ml of methylene chloride containing 25% of methanol, drying, filtering, evaporating to dryness and taking up in 5 ml of ethanol. 2 ml of 1.4 N HCl in ethanol is added, followed by evaporating, leaving to crystallize, separating and washing with ethanol then drying at a temperature of approximately 60° C. In this way 207 mg of expected product is obtained in the form of colourless crystals.

Workup

  1. additionis introduced at ambient temperature under agitation
  2. waitthen left
  3. customto return to ambient temperature
  4. extractionby extracting with 10 ml of methylene chloride containing 25% of methanol
  5. customdrying
  6. filtrationfiltering
  7. customevaporating to dryness
  8. addition2 ml of 1.4 N HCl in ethanol is added
  9. customby evaporating
  10. customleaving
  11. customto crystallize
  12. customseparating
  13. washwashing with ethanol
  14. customthen drying at a temperature of approximately 60° C

Sources & evidence

ORD record
ord-c936872deef543dca63124b424d6f6cd
Source dataset
uspto-grants-2007_04
Patent number
US07208598B2

Reaction notes

Loading…