HCID 178441955, compound → HCID 178441954, compound

HRID 2168657Notes

Reaction equation

HRID 2168657 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][CH:19]=O)[CH2:14][CH2:13]2)=[CH:7][C:6]=1[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:23][CH:22]=1)[CH2:2][CH2:3][CH3:4]>C1COCC1>[CH2:1]([C:5]1[N:10]=[N:9][C:8]([O:11][C@H:12]2[CH2:13][CH2:14][C@H:15]([NH:18][CH3:19])[CH2:16][CH2:17]2)=[CH:7][C:6]=1[C:21]1[CH:22]=[CH:23][C:24]([O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:25][CH:26]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 178441955HCID 178441955, compound

Product 1

HCID 178441954HCID 178441954, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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 reaction
  2. customto come to room temperature
  3. customThe reaction
  4. custommay be quenched with MeOH
  5. customthe solvents may be removed under reduced pressure
  6. customThe crude product may be purified by flash chromatography

Sources & evidence

ORD record
ord-dae270b21c8f46889d39b2521a7bebdf
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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