Ammonia → 6-Chloro-2-fluoro-3-(pivalamidomethyl)benzamide

HRID 59340Notes

Reaction equation

HRID 59340 reaction equation
[Cl:1][C:2]1[C:7]([C:8](O)=[O:9])=[C:6]([F:11])[C:5]([CH2:12][NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH3:26]>C1COCC1>[Cl:1][C:2]1[C:7]([C:8]([NH2:26])=[O:9])=[C:6]([F:11])[C:5]([CH2:12][NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid

Product 1

HCID 900195026-Chloro-2-fluoro-3-(pivalamidomethyl)benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the procedure described in step-2 of Intermediate-26 by using 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (0.400 g, 1.39 mmol), THF (25 mL), oxalyl chloride (0.14 mL, 1.67 mmol) and ammonia gas to afford 0.220 g of the product. 1H NMR (300 MHz, DMSO d6): δ 1.12 (s, 9H), 4.25 (d, J=5.4 Hz, 2H), 7.20 (d, J=8.4 Hz, 1H), 7.30 (d, J=8.4 Hz, 1H), 7.82 (s, 1H), 8.12 (br s, 2H); MS (m/z): 287.01 (M+H+).

Sources & evidence

ORD record
ord-38168a0074a842daa596ae4dd7c0c084
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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