Methanol → HCID 178478731, compound

HRID 1244971Notes

Reaction equation

HRID 1244971 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]([S:31]([NH:34][C:35]3[S:36][CH:37]=[CH:38][N:39]=3)(=[O:33])=[O:32])=[CH:27][CH:26]=2)[N:11]=1.CO>ClCCl>[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[CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:12]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([S:31]([NH:34][C:35]4[S:36][CH:37]=[CH:38][N:39]=4)(=[O:33])=[O:32])=[CH:27][CH:26]=3)[N:11]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 21923052HCID 21923052, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178478731HCID 178478731, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

400 mg of trans-1,4-diaminocyclohexane is taken to approximately 150° C. then 333 mg of the product obtained in Stage 1 above is added, the reaction medium is left under agitation for 3 hours then left to return to ambient temperature and diluted with 30 ml of dichloromethane. 10 ml of methanol is added, followed by washing with 10 ml of water, drying and evaporating the solvents. Chromatography on silica is carried out (eluent: MeOH/NH4OH 98/2), the residue is taken up in an ethanolic solution of hydrochloric acid, followed by evaporating the solvents, impasting in ether, separating, drying under reduced pressure at ambient temperature and 66 mg of expected product is recovered.

Workup

  1. customis taken to approximately 150° C.
  2. waitthen left
  3. customto return to ambient temperature
  4. washby washing with 10 ml of water
  5. customdrying
  6. customevaporating the solvents
  7. customby evaporating the solvents
  8. customseparating
  9. customdrying under reduced pressure at ambient temperature
  10. custom66 mg of expected product is recovered

Sources & evidence

ORD record
ord-9a728296b0c549788d63e07ec63147be
Source dataset
uspto-grants-2006_10
Patent number
US07122669B1

Reaction notes

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