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

HRID 2037019Notes

Reaction equation

HRID 2037019 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]

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-2c531b3b634d48ce83c8c43001749bda
Source dataset
uspto-grants-2013_11
Patent number
US08575177B2

Reaction notes

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