Diisopropylethylamine → HCID 178516596, compound

HRID 1747504Notes

Reaction equation

HRID 1747504 reaction equation
C(N(CC)C(C)C)(C)C.Cl[C:11]1[N:12]=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=1.Cl.[OH:22][C:23]1([C:39]([F:42])([F:41])[F:40])[CH2:28][C:27](=[O:29])[NH:26][C:25]2[NH:30][N:31]=[C:32]([CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)[C:24]1=2>CS(C)=O.C(OCC)(=O)C>[OH:22][C:23]1([C:39]([F:42])([F:41])[F:40])[CH2:28][C:27](=[O:29])[NH:26][C:25]2[NH:30][N:31]=[C:32]([CH:33]3[CH2:34][CH2:35][N:36]([C:11]4[N:12]=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=4)[CH2:37][CH2:38]3)[C:24]1=2

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 282425263-Chloro-6-(trifluoromethyl)pyridazineHCID 178479635HCID 178479635, compound

Product 1

HCID 178516596HCID 178516596, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N,N-Diisopropylethylamine (59.8 μL, 0.352 mmol) and 3-chloro-6-(trifluoromethyl)pyridazine (80.2 mg, 0.439 mmol) were added to a solution of 4-hydroxy-3-(piperidin-4-yl)-4-(trifluoromethyl)-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one hydrochloride (100 mg, 0.293 mmol) produced in Reference Example 60 in dimethyl sulfoxide (0.5 mL), and the mixture was stirred overnight at room temperature. The reaction solution was diluted with ethyl acetate, washed with water, a saturated ammonium chloride aqueous solution, and brine in this order, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: ethyl acetate/methanol=100/0-90/10 (gradient)] to obtain the title compound (39.8 mg, yield: 30%).

Workup

  1. washwashed with water
  2. dry with materiala saturated ammonium chloride aqueous solution, and brine in this order, and dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography [elute: ethyl acetate/methanol=100/0-90/10 (gradient)]

Sources & evidence

ORD record
ord-0e7b5583eb664332b7f81ded0b72e539
Source dataset
uspto-grants-2015_10
Patent number
US09150575B2

Reaction notes

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