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

HRID 2200401Notes

Reaction equation

HRID 2200401 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-55706e70293a4970aac780e338337a7b
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

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