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Potassium Carbonate → (R)-2-(5-cyano-6-(4-cyanophenylamino)pyrazin-2-ylamino)-4-methylpentanamide

HRID 2200439
Notes
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Reaction equation

HRID 2200439 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10]([NH2:12])=[O:11])[CH:5]=[N:4][C:3]=1[C:17]#[N:18].[C:19]([C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1)#[N:20].C([O-])([O-])=O.[K+].[K+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:17]([C:3]1[N:4]=[CH:5][C:6]([NH:8][C@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10]([NH2:12])=[O:11])=[N:7][C:2]=1[NH:25][C:24]1[CH:26]=[CH:27][C:21]([C:19]#[N:20])=[CH:22][CH:23]=1)#[N:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 133964-AminobenzonitrileHCID 634876Binap, (A+-)-HCID 86685528(R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-4-methylpentanamide

Product 1

HCID 86685568(R)-2-(5-cyano-6-(4-cyanophenylamino)pyrazin-2-ylamino)-4-methylpentanamideYield 58.3%

Reagents, catalysts & solvents

2
HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-4-methylpentanamide (75 mg, 0.280 mmol), 4-cyanoaniline (40 mg, 0.339 mmol), K2CO3 (80 mg, 0.579 mmol), BINAP (25 mg, 0.040 mmol) and Pd(OAc)2 (10 mg, 0.044 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 110 C for 2 h. The mixture was concentrated in vacuo. The residue was purified by HPLC to give (R)-2-(5-cyano-6-(4-cyanophenylamino)pyrazin-2-ylamino)-4-methylpentanamide (57 mg).

Workup

  1. customwas degassed with Ar
  2. concentrationThe mixture was concentrated in vacuo
  3. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-482e8cf238b64189b66afb9399c5bc18
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09359308B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes