p-Toluenesulfonic acid monohydrate → HCID 86682990, compound

HRID 1497151Notes

Reaction equation

HRID 1497151 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[CH:3]=1.[CH3:18][O:19][C:20](=[O:29])[CH2:21][C:22](=O)[CH2:23][C:24]([F:27])([F:26])[F:25].[CH3:30]C1C=CC(S(O)(=O)=O)=CC=1.O>>[CH2:18]([O:19][C:20]([C:21]1[C:22]([CH2:23][C:24]([F:27])([F:26])[F:25])=[N:8][C:5]2[C:4]([C:9]=1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[O:29])[CH3:30]

Participants

4

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 53408031Methyl 5,5,5-trifluoro-3-oxopentanoateHCID 86682928HCID 86682928, compound

Product 1

HCID 86682990HCID 86682990, compound

Procedure

The title compound was prepared in analogy to example 10 step B from 4-chloro-2-(2-chloro-phenylethynyl)-phenylamine (prepared as described in example 10 step A, 300 mg, 1.14 mmol), 5,5,5-trifluoro-3-oxo-pentanoic acid methyl ester (prepared as described in example 34 step A, 421.4 mg, 2.29 mmol) and p-TsOH.H2O (326.54 mg, 1.72 mmol). Yellow solid (90 mg, 18% yield). LC-MS: 442 (M+H)+.

Sources & evidence

ORD record
ord-99f2e44b6f854d1b88e558cc95715939
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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