Triethylamine → 8-(Pyrazine-2-carboxamido)-2-(3-(trifluoromethyl)phenyl)quinolin-4-yl acetate

HRID 520463Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7](Cl)=[O:8].[C:10]([O:13][C:14]1[C:23]2[C:18](=[C:19]([NH2:24])[CH:20]=[CH:21][CH:22]=2)[N:17]=[C:16]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)[CH:15]=1)(=[O:12])[CH3:11].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>ClCCl>[C:10]([O:13][C:14]1[C:23]2[C:18](=[C:19]([NH:24][C:7]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][N:1]=3)=[O:8])[CH:20]=[CH:21][CH:22]=2)[N:17]=[C:16]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:32])[F:33])[CH:26]=2)[CH:15]=1)(=[O:12])[CH3:11]

Participants

Conditions

Temperature: 40 °C

Procedure

Pyrazine-2-carbonyl chloride 40 (100 mg) was added to a solution of 8-amino-2-(3-(trifluoromethyl)phenyl)quinolin-4-yl acetate 39 (50 mg, 0.145 mmol) and triethylamine (0.20 mL) in dichloromethane (3 mL). The reaction mixture was stirred at 40° C. for 16 h. The reaction mixture was poured into dilute NaHCO3 (10 mL), and extracted with 3×30 mL dichloromethane. The combined organic layers were dried (MgSO4) and the solvent removed in vacuo. The crude residue was purified by MPLC (97:3 dichloromethane:methanol) to give 41 (33 mg, 50% yield).

Workup

extractionextracted with 3×30 mL dichloromethane
dry with materialThe combined organic layers were dried (MgSO4)
customthe solvent removed in vacuo
customThe crude residue was purified by MPLC (97:3 dichloromethane:methanol)

Sources & evidence

ORD record: ord-9adb244e75dd4372b03916346deac7ab
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326986B2

Reaction notes

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