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

HRID 660433Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:8])[CH2:5][CH2:6]Br)[CH3:2].[NH2:9][C:10]1[N:11]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([CH:26]3[CH2:28][CH2:27]3)=[CH:18][CH:17]=2)[C:12]([SH:15])=[N:13][N:14]=1>CN(C=O)C>[NH2:9][C:10]1[N:11]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([CH:26]3[CH2:28][CH2:27]3)=[CH:18][CH:17]=2)[C:12]([S:15][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:8])=[N:13][N:14]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3-Bromo-propionic acid ethyl ester (158 μL, 224 mg; 1.239 mmol) was added 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). The resulting mixture was 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-38f0261ae2274d34936512b774d20e50
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084483B2

Reaction notes

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