Hydrochloric Acid → HCID 67371488, compound

HRID 2168714Notes

Reaction equation

HRID 2168714 reaction equation
[ClH:1].Cl.[CH:3]1([C:9]2[N:10]=[N:11][C:12]([O:28][CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[CH:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:17][CH:16]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl.[CH2:36](OCC)C>C(Cl)Cl>[ClH:1].[ClH:1].[CH:3]1([C:9]2[N:10]=[N:11][C:12]([O:28][CH:29]3[CH2:30][CH2:31][N:32]([CH3:36])[CH2:33][CH2:34]3)=[CH:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:17][CH:16]=2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67373525HCID 67373525, compound

Product 1

HCID 67371488HCID 67371488, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-cyclohexyl-4-(4-cyclohexyloxy-phenyl)-6-(piperidin-4-yloxy)-pyridazine dihydrochloride (0.079 mmol, 0.04 g) and aqueous formaldehyde (37%, 0.39 mmol, 0.035 mL) in dry DCM (1 mL) was added macroporous resin-bound triacetoxyborohydride (loading 2.36 mmol/gram, 0.47 mmol, 0.20 g). The mixture was shaken for 2 hours. The reaction was placed directly onto a 4 g SiO2 cartridge and the column was eluted with 4-6% (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 (0.5 mL) and DCM (0.5 mL). The volatiles were removed under reduced pressure and the salt was triturated with diethyl ether and filtered to provide the title compound (0.04 g). LCMS: m/z 451 [M+1]. 1H NMR (400 MHz, CD3OD) δ 7.63-7.79 (1 H, m), 7.38-7.43 (2 H, m), 7.10-7.14 (2 H, m), 5.33-5.57 (1 H, m), 4.40-4.51 (1 H, m), 3.66-3.69 (1 H, m), 3.11-3.54 (3 H, m), 2.94 (3 H, s), 2.37-2.62 (2 H, m), 2.20-2.30 (1 H, m), 1.20-2.17 (22 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-004b0112c9b841509ecea5d2eacc29ab
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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