3-Aminoquinoline → (R)-2-(5-cyano-6-(quinolin-3-ylamino)pyrazin-2-ylamino)propanamide

HRID 332726Notes

Reaction equation

HRID 332726 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([CH3:13])[C:10]([NH2:12])=[O:11])[CH:5]=[N:4][C:3]=1[C:14]#[N:15].[NH2:16][C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][CH:21]=2.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:14]([C:3]1[N:4]=[CH:5][C:6]([NH:8][C@H:9]([CH3:13])[C:10]([NH2:12])=[O:11])=[N:7][C:2]=1[NH:16][C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][CH:21]=2)#[N:15]

Participants

7

Reactant 4

HCID 113753-AminoquinolineHCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 86685533(R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)propanamide

Product 1

HCID 86685535(R)-2-(5-cyano-6-(quinolin-3-ylamino)pyrazin-2-ylamino)propanamideYield 51.6%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)propanamide (97 mg, 0.430 mmol), 3-aminoquinoline (62 mg, 0.430 mmol), K2CO3 (100 mg, 0.724 mmol), BINAP (30 mg, 0.048 mmol) and Pd(OAc)2 (15 mg, 0.066 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 110 C for 20 h. The mixture was concentrated in vacuo. The residue was purified by HPLC to give (R)-2-(5-cyano-6-(quinolin-3-ylamino)pyrazin-2-ylamino)propanamide (74 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-3c1a1752ebf94c048048fb432003d779
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Reaction notes

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