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

HRID 1469837Notes

Reaction equation

HRID 1469837 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[C:16]3[C:11](=[C:12]([NH2:17])[CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].[Cl:24][C:25]1[C:30]([C:31](O)=[O:32])=[C:29]([F:34])[C:28]([CH2:35][NH:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:27][CH:26]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:24][C:25]1[C:30]([C:31]([NH:17][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:11]=2[N:10]=[CH:9][CH:8]=[C:7]3[O:6][C:5]2[CH:18]=[CH:19][C:2]([F:1])=[C:3]([C:20]([F:23])([F:21])[F:22])[CH:4]=2)=[O:32])=[C:29]([F:34])[C:28]([CH2:35][NH:36][C:37](=[O:42])[C:38]([CH3:40])([CH3:39])[CH3:41])=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acidHCID 716780484-(4-Fluoro-3-(trifluoromethyl)phenoxy)quinolin-8-amine

Product 1

HCID 716795656-Chloro-2-fluoro-N-(4-(4-fluoro-3-(trifluoromethyl)phenoxy)quinolin-8-yl)-3-(pivalamidomethyl)benzamideYield 32.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using 4-(4-fluoro-3-(trifluoromethyl)phenoxy)quinolin-8-amine (Intermediate-44, 60 mg, 0.18 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 80 mg, 0.27 mmol), oxalyl chloride (52 mg, 0.41 mmol), DMF (1 drop) and DIPEA (70 mg, 0.54 mmol) in CH2Cl2 (2 mL) to afford 35 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.75 (s, 1H), 8.79 (d, J=7.5 Hz, 1H), 8.71 (d, J=5.1 Hz, 1H), 8.16 (t, 1H), 8.09 (d, J=8.7 Hz, 1H), 7.88 (m, 1H), 7.75-7.70 (m, 3H), 7.38 (m, 2H), 6.83 (d, J=5.4 Hz, 1H), 4.32 (d, J=5.1 Hz, 2H), 1.14 (s, 9H); MS (m/z): 592.29 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-db695d5f4cfc424291e93c58407c79d5
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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