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Dimethylformamide → N-(1-(2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-pyrazolo[3,4-f]quinoline-7-car bonyl)piperidin-4-yl)methanesulfonamide

HRID 1844864
Notes
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Reaction equation

HRID 1844864 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([N:10]2[CH:14]([CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:13][C:12](Cl)=[N:11]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl.[NH:22]1[CH2:27][CH2:26][CH:25]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH2:24][CH2:23]1.CCN([CH:39]([CH3:41])C)C(C)C.CN(C(ON1N=N[C:52]2[CH:53]=[CH:54][CH:55]=[N:56][C:51]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN([CH:69]=[O:70])C>C(Cl)Cl>[Cl:1][C:2]1[CH:9]=[C:8]([N:10]2[CH:14]([CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:13]3[C:12]([C:54]4[CH:53]=[CH:52][C:51]([C:69]([N:22]5[CH2:23][CH2:24][CH:25]([NH:28][S:29]([CH3:32])(=[O:30])=[O:31])[CH2:26][CH2:27]5)=[O:70])=[N:56][C:55]=4[CH2:39][CH2:41]3)=[N:11]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 20569935N-(piperidin-4-yl)methanesulfonamide hydrochlorideHCID 666826842-chloro-4-(3-chloro-5-cyclopentyl-4,5-dihydro-1H-pyrazole-1-yl)benzonitrile

Product 1

HCID 56849167N-(1-(2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-pyrazolo[3,4-f]quinoline-7-car bonyl)piperidin-4-yl)methanesulfonamideYield 91.74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a dried reaction flask, 2-chloro-4-(3-chloro-5-cyclopentyl-4,5-dihydro-1H-pyrazole-1-yl)benzonitrile (420 mg, 1 mmol), N-piperidine-4-ylmethanesulfonamide hydrochloride (280 mg, 1.30 mmol), DIEA (0.52 mL, 3 mmol), and HATU (418 mg, 1.1 mmol) were added to a mixed solvent of CH2Cl2 (10 mL) and DMF (5 mL). The mixture was stirred at room temperature for 3 hr. LC-MS monitored that the starting materials vanished. The solution was evaporated at reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate. The combined organic phase was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to produce a yellow powdery solid, which was washed with water and anhydrous ethyl ether to obtain a yellow powdery solid (532 mg) in 91.74% yield.

Workup

  1. customThe solution was evaporated at reduced pressure
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined organic phase was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto produce a yellow powdery solid, which
  8. washwas washed with water and anhydrous ethyl ether

Sources & evidence

ORD record
ord-f081dc93eadf46adbc0529fbd546f522
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946279B2

Reaction notes

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