2-[(Pyrrolidin-1-yl)methyl]-1,3-benzoxazol-5-amine → 3-(2-chloro-4-trifluoromethylphenyl)propynoic Acid (2-pyrrolidin-1-ylmethylbenzoxazol-5-yl)amide

HRID 735101Notes

Reaction equation

HRID 735101 reaction equation
[N:1]1([CH2:6][C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:10]=3[N:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:17][C:18]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:19]=1[C:28]#[C:29][C:30](O)=[O:31]>ClCCl.CO>[N:1]1([CH2:6][C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([NH:16][C:30](=[O:31])[C:29]#[C:28][C:19]4[CH:20]=[CH:21][C:22]([C:24]([F:26])([F:25])[F:27])=[CH:23][C:18]=4[Cl:17])=[CH:12][C:10]=3[N:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 597669972-[(Pyrrolidin-1-yl)methyl]-1,3-benzoxazol-5-amineHCID 68817422(2-Chloro-4-trifluoromethylphenyl)propynoic acid

Product 1

HCID 578457423-(2-chloro-4-trifluoromethylphenyl)propynoic Acid (2-pyrrolidin-1-ylmethylbenzoxazol-5-yl)amide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 2.3.f. from 0.2 g (0.92 mmol) of 2-pyrrolidin-1-ylmethylbenzoxazol-5-ylamine and 0.2 g (0.8 mmol) of (2-chloro-4-trifluoromethylphenyl)propynoic acid. Yield: 290 mg (81% of theory); C22H17ClF3N3O2 (M=447.84); melting point: 218° C.-223° C.; calc.: molecular ion peak (M+H)+: 448/450 (Cl); found: molecular ion peak (M+H)+: 448/450 (Cl); Rf value: 0.33 (silica gel, dichloromethane/methanol (19:1)).

Workup

  1. customPrepared analogously to Example 2.3.f

Sources & evidence

ORD record
ord-b180f209dbdd426fab81be89cbf51b24
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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