Ethyl 3-bromopropionate → ethyl 3-(5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)propanoate

HRID 473252Notes

Reaction equation

[NH2:1][C:2]1[N:3]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH:18]3[CH2:20][CH2:19]3)=[CH:10][CH:9]=2)[C:4]([SH:7])=[N:5][N:6]=1.[CH2:21]([O:23][C:24](=[O:28])[CH2:25][CH2:26]Br)[CH3:22]>CN(C=O)C>[NH2:1][C:2]1[N:3]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH:18]3[CH2:20][CH2:19]3)=[CH:10][CH:9]=2)[C:4]([S:7][CH2:26][CH2:25][C:24]([O:23][CH2:21][CH3:22])=[O:28])=[N:5][N:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 5-Amino-4-(4-cyclopropyl-naphthalen-1-yl)-4H-[1,2,4]triazole-3-thiol (0.35 g, 1.239 mmol) in DMF (2.5 mL) was added 3-Bromo-propionic acid ethyl ester (158 μL, 224 mg; 1.239 mmol) and heated to 60° C. for 20 hours. The reaction mixture was concentrated and sonicated with ethyl ether several times, decanting the ethyl ether layer. The resulting light yellow oil was placed on high vacuum to afford crude ethyl 3-(5-amino-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)propanoate as a light brown oily foam which was used directly in the next step (0.409 g, 87%).

Workup

concentrationThe reaction mixture was concentrated
customsonicated with ethyl ether several times
customdecanting the ethyl ether layer

Sources & evidence

ORD record: ord-199ed947119b4faca2dfa1cafb70492b
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633232B2

Reaction notes

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