Ammonia methanol dichloromethane → HCID 57845718, compound

HRID 735147Notes

Reaction equation

HRID 735147 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]#[C:13][C:14]([OH:16])=O.[NH2:17][C:18]1[CH:35]=[CH:34][C:21]([O:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH:28]([C:31]([NH2:33])=[O:32])[CH2:27][CH2:26]2)=[C:20]([O:36][CH3:37])[CH:19]=1.ClCCl.CO.N>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=1[C:12]#[C:13][C:14]([NH:17][C:18]1[CH:35]=[CH:34][C:21]([O:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH:28]([C:31]([NH2:33])=[O:32])[CH2:27][CH2:26]2)=[C:20]([O:36][CH3:37])[CH:19]=1)=[O:16]

Participants

4

Reactant 3

HCID 21584172Ammonia methanol dichloromethaneHCID 68817417HCID 68817417, compoundHCID 68817422(2-Chloro-4-trifluoromethylphenyl)propynoic acid

Product 1

HCID 57845718HCID 57845718, compound

Procedure

Prepared analogously to Example 2.3.f. from 150 mg (0.6 mmol) of (2-chloro-4-trifluoromethylphenyl)propynoic acid and 194 mg (0.66 mmol) of 1-[2-(4-amino-2-methoxyphenoxy)ethyl]piperidine-4-carboxylic acid amide. Yield: 310 mg (98% of theory); melting point: 150° C.; C25H25ClF3N3O4 (M=523.93); calc.: molecular ion peak (M+H)+: 524/526 (Cl); found: molecular ion peak (M+H)+: 524/526 (Cl); Rf value: 0.4 (silica gel, dichloromethane/methanol/ammonia (9:1:0.1)).

Workup

  1. customPrepared analogously to Example 2.3.f

Sources & evidence

ORD record
ord-f5b4c26f710f4c4c988819ddc8efee79
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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