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

HRID 2200467Notes

Reaction equation

HRID 2200467 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([NH2:12])=[O:11])[CH:5]=[N:4][C:3]=1[C:20]#[N:21].[NH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[CH:28][CH:27]=[CH:26]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:20]([C:3]1[N:4]=[CH:5][C:6]([NH:8][C@H:9]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([NH2:12])=[O:11])=[N:7][C:2]=1[NH:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[CH:28][CH:27]=[CH:26]2)#[N:21]

Participants

7

Reactant 4

HCID 113736-AminoquinolineHCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 86685588(R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-3-phenylpropanamide

Product 1

HCID 86685589(R)-2-(5-cyano-6-(quinolin-6-ylamino)pyrazin-2-ylamino)-3-phenylpropanamideYield 12.1%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-3-phenylpropanamide (128 mg, 0.424 mmol), 6-aminoquinoline (80 mg, 0.555 mmol), K2CO3 (100 mg, 0.724 mmol), BINAP (30 mg, 0.048 mmol) and Pd(OAc)2 (15 mg, 0.066 mmol) in dioxane (3 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-6-ylamino)pyrazin-2-ylamino)-3-phenylpropanamide (21 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-4a4147891c224d079cceae47a9786738
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

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