3-(2,4-dichlorophenyl)prop-2-ynoic acid → 3-(2,4-Dichlorophenyl)propynoic acid-[2-(2-pyrrolidin-1-ylethyl)benzoxazol-5-yl]amide

HRID 735099Notes

Reaction equation

HRID 735099 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][CH2:11][N:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)=[N:7][C:6]=2[CH:17]=1.[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[C:26]#[C:27][C:28](O)=[O:29].ClCCl.CO.N>>[N:12]1([CH2:11][CH2:10][C:8]2[O:9][C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:28](=[O:29])[C:27]#[C:26][C:20]4[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=4[Cl:18])=[CH:17][C:6]=3[N:7]=2)[CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

4

Reactant 3

HCID 2285093-(2,4-dichlorophenyl)prop-2-ynoic acidHCID 21584172Ammonia methanol dichloromethaneHCID 688179455-Amino-2-(2-pyrrolidin-1-ylethyl)benzoxazole

Product 1

HCID 578457453-(2,4-Dichlorophenyl)propynoic acid-[2-(2-pyrrolidin-1-ylethyl)benzoxazol-5-yl]amide

Procedure

Prepared analogously to Example 3.1.e. from 5-amino-2-(2-pyrrolidin-1-ylethyl)benzoxazole and (2,4-dichlorophenyl)propynoic acid. Yield: 43 mg (33.1% of theory); C22H19Cl2N3O2 (M=428.32); melting point: 130° C.; calc.: molecular ion peak (M+H)+: 428/430/432; found: molecular ion peak (M+H)+: 428/430/432; C13H17N3O (M=231.30); calc.: molecular ion peak (M+H)+: 232; found: molecular ion peak (M+H)+: 232; Rf value: 0.21 (silica gel, dichloromethane/methanol/ammonia (10:1:0.1)).

Workup

  1. customPrepared analogously to Example 3.1.e

Sources & evidence

ORD record
ord-7ad0d630371542c2999960ab71f53ac4
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

Loading…