6-Aminoquinoline → HCID 86685597, compound

HRID 332805Notes

Reaction equation

HRID 332805 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2([C:13]([NH2:15])=[O:14])[CH2:12][CH2:11][CH2:10]2)[CH:5]=[N:4][C:3]=1[C:16]#[N:17].[NH2:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]=[CH:24][CH:23]=[CH:22]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:16]([C:3]1[N:4]=[CH:5][C:6]([NH:8][C:9]2([C:13]([NH2:15])=[O:14])[CH2:12][CH2:11][CH2:10]2)=[N:7][C:2]=1[NH:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]=[CH:24][CH:23]=[CH:22]2)#[N:17]

Participants

7

Reactant 4

HCID 113736-AminoquinolineHCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 86685596HCID 86685596, compound

Product 1

HCID 86685597HCID 86685597, compoundYield 32%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 1-(6-chloro-5-cyanopyrazin-2-ylamino)cyclobutanecarboxamide (22 mg, 0.087 mmol), 6-aminoquinoline (30 mg, 0.208 mmol), K2CO3 (90 mg, 0.652 mmol), BINAP (25 mg, 0.040 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 5 h. The mixture was concentrated in vacuo. The residue was purified by HPLC to give 1-(5-cyano-6-(quinolin-6-ylamino)pyrazin-2-ylamino)cyclobutanecarboxamide (10 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-602424a693d94763ac74910d67a546ef
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Reaction notes

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