Triethylamine → HCID 178511610, compound

HRID 22939Notes

Reaction equation

HRID 22939 reaction equation
C(OC([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16]2[N:17]=[N:18][C:19](Cl)=[CH:20][CH:21]=2)[CH2:11][CH2:10]1)=O)(C)(C)C.C(N(CC)CC)C>C(O)C.O1CCCC1.[C].[Pd]>[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([NH:15][C@H:12]2[CH2:13][CH2:14][C@H:9]([NH2:8])[CH2:10][CH2:11]2)[N:17]=1

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 178453998HCID 178453998, compound

Product 1

HCID 178511610HCID 178511610, compoundYield 61.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In the mixed solvent of 5 ml of ethanol and 4 ml of tetrahydrofuran were dissolved 168 mg of N-tert-butoxycarbonyl-trans-4-[(6-chloro-3-pyridazinyl)amino]cyclohexylamine (Reference Example 3-46) and 0.5 ml of triethylamine. To the solution was added 50 mg of 10% palladium carbon and the mixture was stirred under hydrogen atmosphere with normal pressure at room temperature for 1 day. After the catalyst was removed by filtration, the solvent was removed, and the residue was stirred in 2 ml of trifluoroacetic acid for 3 hours. The solvent was removed, an aqueous 10% sodium hydroxide solution was added to the residue, the mixture was extracted with chloroform and dried over anhydrous sodium sulfate. Subsequently, the solvent was removed under reduced pressure to obtain 61 mg of trans-4-(pyridazin-3-ylamino)cyclohexylamine (Reference Example 3-48 in Table 5).

Workup

  1. customAfter the catalyst was removed by filtration
  2. customthe solvent was removed
  3. stirringthe residue was stirred in 2 ml of trifluoroacetic acid for 3 hours
  4. customThe solvent was removed
  5. additionan aqueous 10% sodium hydroxide solution was added to the residue
  6. extractionthe mixture was extracted with chloroform
  7. dry with materialdried over anhydrous sodium sulfate
  8. customSubsequently, the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8493df4dcd214e50a9c2df681bf13ec0
Source dataset
uspto-grants-2005_02
Patent number
US06849622B2

Reaction notes

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