Oxalyl chloride → 6-Chloro-2-fluoro-3-(pivalamidomethyl)-N-(4-((3-(trifluoromethyl)phenyl)amino)quinolin-8-yl)benzamide

HRID 1469824Notes

Reaction equation

HRID 1469824 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[C:15]([NH2:20])[CH:16]=[CH:17][CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:7][CH:8]=1.[Cl:23][C:24]1[C:29]([C:30](O)=[O:31])=[C:28]([F:33])[C:27]([CH2:34][NH:35][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:26][CH:25]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:23][C:24]1[C:29]([C:30]([NH:20][C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:14]=2[N:13]=[CH:12][CH:11]=[C:10]3[NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:4]=2)=[O:31])=[C:28]([F:33])[C:27]([CH2:34][NH:35][C:36](=[O:41])[C:37]([CH3:39])([CH3:38])[CH3:40])=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acidHCID 86692281N-(3-(trifluoromethyl)phenyl)quinoline-4,8-diamine

Product 1

HCID 866922886-Chloro-2-fluoro-3-(pivalamidomethyl)-N-(4-((3-(trifluoromethyl)phenyl)amino)quinolin-8-yl)benzamideYield 10.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using N4-(3-(trifluoromethyl)phenyl)quinoline-4,8-diamine (Intermediate-25, 100 mg, 0.33 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 190 mg, 0.66 mmol), oxalyl chloride (125 mg, 0.99 mmol), DMF (1 drop) and DIPEA (128 mg, 0.99 mmol) in CH2Cl2 (6 mL) to afford 20 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.62 (s, 1H), 9.35 (s, 1H), 8.73-8.71 (d, J=7.2 Hz, 1H), 8.52 (d, 1H), 8.17 (m, 2H), 7.71-7.62 (m, 4H), 7.48-7.36 (m, 3H), 7.14 (m, 1H), 4.31 (d, 2H), 1.14 (s, 9H); MS (m/z): 573.36 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-7691c19e2de549748c75321288447eba
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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