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

HRID 1469849Notes

Reaction equation

HRID 1469849 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[C:9]([NH2:14])[CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1)[CH3:2].[Cl:15][C:16]1[C:21]([C:22](O)=[O:23])=[C:20]([F:25])[C:19]([CH2:26][NH:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:18][CH:17]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:15][C:16]1[C:21]([C:22]([NH:14][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:8]=2[N:7]=[CH:6][CH:5]=[C:4]3[O:3][CH2:1][CH3:2])=[O:23])=[C:20]([F:25])[C:19]([CH2:26][NH:27][C:28](=[O:33])[C:29]([CH3:31])([CH3:30])[CH3:32])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acidHCID 682812844-Ethoxyquinolin-8-amine

Product 1

HCID 866923026-Chloro-N-(4-ethoxyquinolin-8-yl)-2-fluoro-3-(pivalamidomethyl)benzamideYield 23.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using 4-ethoxyquinolin-8-amine (Intermediate-56, 80 mg, 0.425 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 159 mg, 0.553 mmol), oxalyl chloride (162 mg, 1.27 mmol), DMF (1 drop) and DIPEA (219 mg, 1.7 mmol) in CH2Cl2 (2 mL) to afford 46 mg of the title product. 1H NMR (400 MHz, DMSO-d6): δ 10.59 (s, 1H), 8.71-8.68 (m, 2H), 8.13 (t, 1H), 7.93-7.90 (dd, J=1.2, 8.4 Hz, 1H), 7.61-7.57 (t, J=8.0 Hz, 1H), 7.42-7.40 (d, J=8.4 Hz, 1H), 7.36-7.23 (t, J=8.0 Hz, 1H), 7.12-7.11 (d, J=5.2 Hz, 1H), 4.35-4.29 (m, 4H), 1.50-1.47 (t, J=7.2 Hz, 3H), 1.14 (s, 9H); MS (m/z): 458.24 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-52ea0922ee4b46169e739d5c04924617
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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