HCID 21923031, compound → HCID 178478730, compound

HRID 1272667Notes

Reaction equation

HRID 1272667 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:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[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:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)[N:11]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 21923031HCID 21923031, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178478730HCID 178478730, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

740 mg of trans-1,4-diaminocyclohexane is taken to approximately 150° C. then 466 mg of the product obtained in Stage 1 above is added, the reaction medium is maintained under agitation at 140° C. for 6 hours then left to return to ambient temperature. Then 15 ml of water is added, followed by extracting with dichloromethane, drying and evaporating the solvent. The residue is chromatographed on silica (eluent: MeOH/NH4OH 98/2), 270 mg of the product obtained is removed and taken up in 10 ml of ethanol, 6 ml of an ethanolic solution of hydrochloric acid is added, followed by separating, washing with ether, drying under reduced pressure at 60° C. and 79 mg of expected product is recovered.

Workup

  1. customis taken to approximately 150° C.
  2. waitthen left
  3. customto return to ambient temperature
  4. extractionby extracting with dichloromethane
  5. customdrying
  6. customevaporating the solvent
  7. customThe residue is chromatographed on silica (eluent: MeOH/NH4OH 98/2), 270 mg of the product
  8. customobtained
  9. customis removed
  10. addition6 ml of an ethanolic solution of hydrochloric acid is added
  11. customby separating
  12. washwashing with ether
  13. customdrying under reduced pressure at 60° C.
  14. custom79 mg of expected product is recovered

Sources & evidence

ORD record
ord-062c85a71df6484b9fe10d5c6fc1cf91
Source dataset
uspto-grants-2007_04
Patent number
US07208598B2

Reaction notes

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