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1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-(4-(Cyanomethyl)tetrahydro-2H-thiopyran-4-yl)-3-((4-fluorophenyl)amino)-1H-pyrazole-4-carboxamide

HRID 521213
Notes
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Reaction equation

HRID 521213 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:13]([C:14]([NH2:16])=[O:15])=[CH:12][NH:11][N:10]=2)=[CH:4][CH:3]=1.O=[S:18]1(=O)[CH2:23][CH2:22][C:21](=[CH:24][C:25]#[N:26])[CH2:20][CH2:19]1.C1CCN2C(=NCCC2)CC1>CC#N>[C:25]([CH2:24][C:21]1([N:11]2[CH:12]=[C:13]([C:14]([NH2:16])=[O:15])[C:9]([NH:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[N:10]2)[CH2:22][CH2:23][S:18][CH2:19][CH2:20]1)#[N:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 617011612-(1,1-dioxidodihydro-2H-thiopyran-4(3H)-ylidene)acetonitrileHCID 178513765HCID 178513765, compound2×

Product 1

HCID 715359871-(4-(Cyanomethyl)tetrahydro-2H-thiopyran-4-yl)-3-((4-fluorophenyl)amino)-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
80 °C

Procedure

3-[(4-Fluorophenyl)amino]-1H-pyrazole-4-carboxamide (Intermediate 31-7) (100 mg, 0.45 mmol) was added to a mixture of 2-(1,1-dioxidodihydro-2H-thiopyran-4(3H)-ylidene)acetonitrile (160 mg, 0.91 mmol) in MeCN (1.51 mL). DBU (0.068 mL, 0.45 mmol) was then added, the reaction vessel was capped and the reaction mixture was heated to 80° C. for 4 hours. The reaction mixture was cooled to ambient temperature, and purified by reverse phase preparative HPLC (using a gradient elution of MeCN/water, with 0.1% v/v TFA modifier). Desired fractions were combined, basified with saturated aqueous NaHCO3, and extracted with EtOAc. The organic layer was dried over anhydrous NaSO4, filtered, and concentrated in vacuo to afford the title compound, Example #7.

Workup

  1. customthe reaction vessel was capped
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. custompurified by reverse phase preparative HPLC (
  4. washa gradient elution of MeCN/water
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer was dried over anhydrous NaSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-94be6161e58f4709bfb7180c0d923dd9
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09328099B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes