p-Toluenesulfonic acid → 3-(3-(1,2,4-Oxadiazol-3-yl)phenethoxy)-N-cyclohexyl-N-(2-oxoethyl)propanamide

HRID 909912Notes

Reaction equation

HRID 909912 reaction equation
[O:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:7]=[C:8]([CH:29]=[CH:30][CH:31]=2)[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]([N:16]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:17][CH:18](OC)[O:19]C)=[O:15])=[N:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN1C(=O)CCC1>[O:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:7]=[C:8]([CH:29]=[CH:30][CH:31]=2)[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]([N:16]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:17][CH:18]=[O:19])=[O:15])=[N:2]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 592903753-(3-(1,2,4-Oxadiazol-3-yl)phenethoxy)-N-cyclohexyl-N-(2,2-dimethoxyethyl)propanamide

Product 1

HCID 866412603-(3-(1,2,4-Oxadiazol-3-yl)phenethoxy)-N-cyclohexyl-N-(2-oxoethyl)propanamide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To 3-(3-(1,2,4-oxadiazol-3-yl)phenethoxy)-N-cyclohexyl-N-(2,2-dimethoxyethyl)propanamide [Example 11, Step ii)] (500 mg) in NMP (4 mL) was added p-toluenesulfonic acid (441 mg) and the mixture stirred for 8 h. After work-up the material was used in the next step directly.

Sources & evidence

ORD record
ord-87d22aded8914e95a8b783841780ea93
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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