Hydrochloric Acid → {4-[6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-cyclohexyl}-methyl-amine dihydrochloride

HRID 401930Notes

Reaction equation

HRID 401930 reaction equation
[CH2:1]([C:5]1[N:10]=[N:9][C:8]([O:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([NH:18][CH3:19])[CH2:14][CH2:13]2)=[CH:7][C:6]=1[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:22][CH:21]=1)[CH2:2][CH2:3][CH3:4].[ClH:33]>C(OCC)C.C(Cl)Cl>[ClH:33].[ClH:33].[CH2:1]([C:5]1[N:10]=[N:9][C:8]([O:11][CH:12]2[CH2:13][CH2:14][CH:15]([NH:18][CH3:19])[CH2:16][CH2:17]2)=[CH:7][C:6]=1[C:20]1[CH:21]=[CH:22][C:23]([O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:24][CH:25]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178441954HCID 178441954, compound

Product 1

HCID 67375692{4-[6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-cyclohexyl}-methyl-amine dihydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of trans-N-{4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-cyclohexyl}-formamide in anhydrous THF at 0° C. may be treated with borane-THF complex in THF (1 M, excess). The reaction may be allowed to come to room temperature and may be monitored by LCMS until the reaction is complete. The reaction may be quenched with MeOH and the solvents may be removed under reduced pressure. The crude product may be purified by flash chromatography using with 1-5% (2N NH3 in MeOH) in DCM to give trans-{4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-cyclohexyl}-methyl-amine. The neutral amine may be treated with 2N HCl in diethyl ether and DCM. The volatiles may be removed under reduced pressure and the salt may be triturated with diethyl ether and filtered to provide the title compound. LCMS: m/z 439 [M+1].

Workup

  1. customThe volatiles may be removed under reduced pressure
  2. customthe salt may be triturated with diethyl ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-7d37dfaa89c241da93333e1b32476d57
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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