1,4-Dioxane hydrochloride → (+/-)-cis-6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid (3-fluoro-1-methyl-piperidin-4-ylmethyl)-amide dihydrochloride

HRID 1972085Notes

Reaction equation

HRID 1972085 reaction equation
[F:1][C@H:2]1[C@@H:7]([CH2:8][NH:9][C:10]([C:12]2[N:13]=[N:14][C:15]([CH2:31][CH2:32][CH2:33][CH3:34])=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:20][CH:19]=3)[CH:17]=2)=[O:11])[CH2:6][CH2:5][N:4]([CH3:35])[CH2:3]1.[ClH:36].O1CCOCC1>>[ClH:36].[ClH:36].[F:1][C@H:2]1[C@@H:7]([CH2:8][NH:9][C:10]([C:12]2[N:13]=[N:14][C:15]([CH2:31][CH2:32][CH2:33][CH3:34])=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:20][CH:19]=3)[CH:17]=2)=[O:11])[CH2:6][CH2:5][N:4]([CH3:35])[CH2:3]1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 58438382(+/-)-cis-6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid (3-fluoro-1-methyl-piperidin-4-ylmethyl)-amide

Product 1

HCID 131730544(+/-)-cis-6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid (3-fluoro-1-methyl-piperidin-4-ylmethyl)-amide dihydrochloride

Procedure

(±)-cis-6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid (3-fluoro-1-methyl-piperidin-4-ylmethyl)-amide (0.35 mmol, 160 mg) was stirred in 4 M HCl/dioxane (1 mL) for 20 min at room temperature. After evaporating the solvent, dichloromethane (0.2 mL) and hexane (1 mL) was added to precipitate (±)-cis-6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid (3-fluoro-1-methyl-piperidin-4-ylmethyl)-amide dihydrochloride. LCMS: m/z 484 [M+1]. 1H NMR (400 MHz, CD3OD) δ 8.51 (1H, s), 7.50-7.51 (2H, m), 7.13-7.15 (2H, m), 4.44-4.48 (1H, m), 3.43-3.76 (5H, m), 2.97-3.03 (1H, m), 2.89-2.90 (3H, m), 2.80-2.85 (1H, m), 2.08-2.34 (1H, m), 1.99-2.04 (2H, m), 1.81-1.84 (3H, m), 1.30-1.63 (13H, m), 0.83-0.87 (3H, t).

Workup

  1. customAfter evaporating the solvent, dichloromethane (0.2 mL) and hexane (1 mL)
  2. additionwas added
  3. customto precipitate (±)-cis-6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid (3-fluoro-1-methyl-piperidin-4-ylmethyl)-amide dihydrochloride

Sources & evidence

ORD record
ord-174160113821437ea65de34f651314de
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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