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Water → 3-chloro-4-[7-(cyclopropylamino)-3-[(Z)-(2,5-dioxoimidazolidin-4-ylidene)methyl]pyrazolo[1,5-a]pyrimidin-5-yl]oxybenzonitrile

HRID 624801
Notes
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Reaction equation

HRID 624801 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]([CH:16]2[CH2:18][CH2:17]2)C(=O)OC(C)(C)C)[N:5]2[N:19]=[CH:20][C:21](/[CH:22]=[C:23]3\[NH:24][C:25](=[O:29])[NH:26][C:27]\3=[O:28])=[C:4]2[N:3]=1.[Cl:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=1[OH:39])[C:34]#[N:35].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=1[O:39][C:2]1[CH:7]=[C:6]([NH:8][CH:16]2[CH2:18][CH2:17]2)[N:5]2[N:19]=[CH:20][C:21](/[CH:22]=[C:23]3\[NH:24][C:25](=[O:29])[NH:26][C:27]\3=[O:28])=[C:4]2[N:3]=1)[C:34]#[N:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2735739Benzonitrile, 3-chloro-4-hydroxy-HCID 86714615HCID 86714615, compound

Product 1

HCID 1785100813-chloro-4-[7-(cyclopropylamino)-3-[(Z)-(2,5-dioxoimidazolidin-4-ylidene)methyl]pyrazolo[1,5-a]pyrimidin-5-yl]oxybenzonitrileYield 57.4%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Procedure

(Z)-tert-butyl 5-chloro-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate (75 mg, 0.18 mmol) was dissolved in anhydrous DMF (0.6 mL). 3-chloro-4-hydroxybenzonitrile (41 mg, 0.27 mmol) and K2CO3 (75 mg, 0.54 mmol) were added. After 24 h, H2O (3.5 mL) was added to the reaction and the bright yellow precipitate was filtered and dried. The crude solid was dissolved in dichloromethane (1 mL) and trifluoroacetic acid (1 mL). After 1 h, the reaction was concentrated to dryness and the residue was triturated with Et2O (3 mL) and filtered to provide (Z)-3-chloro-4-(7-(cyclopropylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-5-yloxy)benzonitrile (45 mg, 57% over two steps) as a bright yellow solid.

Workup

  1. filtrationthe bright yellow precipitate was filtered
  2. customdried
  3. dissolutionThe crude solid was dissolved in dichloromethane (1 mL)
  4. waitAfter 1 h
  5. concentrationthe reaction was concentrated to dryness
  6. customthe residue was triturated with Et2O (3 mL)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-b0e31d6debac4f8f9883c227656dab37
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09303033B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes