Hydrochloric Acid → HCID 67372267, compound

HRID 2168721Notes

Reaction equation

HRID 2168721 reaction equation
[ClH:1].Cl.[CH:3]1([C:7]2[N:8]=[N:9][C:10]([O:26][CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:15][CH:14]=2)[CH2:6][CH2:5][CH2:4]1.Cl.[CH2:34](OCC)C>C(Cl)Cl>[ClH:1].[ClH:1].[CH:3]1([C:7]2[N:8]=[N:9][C:10]([O:26][CH:27]3[CH2:28][CH2:29][N:30]([CH3:34])[CH2:31][CH2:32]3)=[CH:11][C:12]=2[C:13]2[CH:14]=[CH:15][C:16]([O:19][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)=[CH:17][CH:18]=2)[CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67372091HCID 67372091, compound

Product 1

HCID 67372267HCID 67372267, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-cyclobutyl-4-(4-cyclohexyloxy-phenyl)-6-(piperidin-4-yloxy)-pyridazine dihydrochloride (0.17 mmol, 0.08 g) and aqueous formaldehyde (37%, 0.83 mmol, 0.07 mL) in dry DCM (1 mL) was added macroporous resin-bound triacetoxyborohydride (loading 2.36 mmol/gram, 1.0 mmol, 0.42 g). The mixture was shaken for 12 hours. The reaction was placed directly onto a 4 g SiO2 cartridge and the column was eluted with 0-6% (2N NH3 in MeOH) in DCM to give 3-cyclohexyl-4-(4-cyclohexyloxy-phenyl)-6-(1-methyl-piperidin-4-yloxy)-pyridazine. The neutral amine was treated with 2N HCl in diethyl ether (1 mL) and DCM (1 mL). The volatiles were removed under reduced pressure and the salt was triturated with diethyl ether and filtered to provide the title compound (0.05 g). LCMS: m/z 423 [M+1]. 1H NMR (400 MHz, CD3OD) δ 7.26-7.47 (3 H, m), 7.02-7.11 (2 H, m), 5.35-5.60 (1 H, m), 4.37-4.48 (1 H, m), 3.97-4.13 (1 H, m), 3.67 (1 H, d), 3.23-3.53 (2 H, m), 2.92 (3 H, s), 1.95-2.62 (12 H, m), 1.75-1.92 (3 H, m), 1.29-1.68 (6 H, m).

Workup

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

Sources & evidence

ORD record
ord-aebb308d7e8041af89b329f8de2d1132
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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