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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1469836Generated: October 30, 2026

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

https://huagongshe.com/reaction/1469836

Reaction equation

Participants

RoleNameHCIDCharge
ReactantOxalyl chlorideHCID 65578—
ReactantDiisopropylethylamineHCID 81531—
ReactantHCID 71678385HCID 71678385—
Reactant4-(3-(Trifluoromethyl)phenoxy)quinazolin-8-amineHCID 71680391—
CatalystDimethylformamideHCID 6228—
SolventDichloromethaneHCID 6344—
Product6-Chloro-2-methoxy-3-(pivalamidomethyl)-N-(4-(3-(trifluoromethyl)phenoxy)quinazolin-8-yl)benzamideHCID 7167956232.3%

Reaction Steps

The title compound was prepared following the procedure described in Example-1 using 4-(3-(trifluoromethyl)phenoxy)quinazolin-8-amine (Intermediate-8, 60 mg, 0.19 mmol), 6-chloro-2-methoxy-3-(pivalamidomethyl)benzoic acid (Intermediate-43, 88 mg, 0.29 mmol), oxalyl chloride (55 mg, 0.44 mmol), DMF (1 drop) and DIPEA (74 mg, 0.57 mmol) in CH2Cl2 (2 mL) to afford 36 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.49 (s, 1H), 8.92 (d, J=7.8 Hz, 1H), 8.77 (s, 1H), 8.17-8.11 (m, 2H), 7.86 (m, 2H), 7.74 (m, 3H), 7.30 (m, 2H), 4.29 (d, 2H), 3.84 (s, 3H), 1.15 (s, 9H); MS (m/z): 587.17 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09006257B2
Source datasetuspto-grants-2015_04
ORD IDord-17faab2e2f004d1fba865894b36425fd
Source noteuspto-grants-2015_04