HCID 21923073, compound → HCID 178478728, compound

HRID 1272668Notes

Reaction equation

HRID 1272668 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]([C:31]([F:34])([F:33])[F: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]([C:31]([F:32])([F:34])[F:33])=[CH:27][CH:26]=3)[N:11]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 21923073HCID 21923073, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178478728HCID 178478728, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

684 mg of trans-1,4-diaminocyclohexane is taken to approximately 150° C. then 229 mg of the product obtained in Stage 1 above is added, the reaction medium is maintained under agitation at 140° C. for 5 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), 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 159 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)
  8. addition6 ml of an ethanolic solution of hydrochloric acid is added
  9. customby separating
  10. washwashing with ether
  11. customdrying under reduced pressure at 60° C.
  12. custom159 mg of expected product is recovered

Sources & evidence

ORD record
ord-02c9adb702674847b69b83554161d928
Source dataset
uspto-grants-2007_04
Patent number
US07208598B2

Reaction notes

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