HCID 21923039, compound → HCID 178478686, compound

HRID 1272666Notes

Reaction equation

HRID 1272666 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:32]=[CH:31][C:28]([C:29]#[N: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]#[N:30])=[CH:31][CH:32]=3)[N:11]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 21923039HCID 21923039, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178478686HCID 178478686, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

2 g of trans-1,4-diaminocyclohexane is taken to approximately 150° C. then 1.18 g of the product obtained in Stage 1 above is added, the reaction medium is maintained under agitation to 140° C. for 6 hours then left to return to ambient temperature. Then 30 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), 130 mg of the product obtained is removed and taken up in 10 ml of ethanol, 4 ml of an ethanolic solution of hydrochloric acid is added, followed by separating, washing with ether, drying under reduced pressure at 50° C. and 144 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), 130 mg of the product
  8. customobtained
  9. customis removed
  10. addition4 ml of an ethanolic solution of hydrochloric acid is added
  11. customby separating
  12. washwashing with ether
  13. customdrying under reduced pressure at 50° C.
  14. custom144 mg of expected product is recovered

Sources & evidence

ORD record
ord-7c97db92df4546aaa2c47b10ff28261b
Source dataset
uspto-grants-2007_04
Patent number
US07208598B2

Reaction notes

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