N,N'-Dimethylethylenediamine → HCID 24989848, compound

HRID 643020Notes

Reaction equation

[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[N:13][N:14]([C:16]3[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1.C([N:30]1[CH2:35][CH2:34][NH:33][C:32](=[O:36])[CH2:31]1)(OC(C)(C)C)=O.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.[Cu]I>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[N:13][N:14]([C:16]3[CH:21]=[CH:20][C:19]([N:33]4[CH2:34][CH2:35][NH:30][CH2:31][C:32]4=[O:36])=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide (100 mg, 0.22 mmol), 4-N-Boc-2-oxo-piperazine (88 mg, 0.44 mmol), CuI (13 mg, 0.066 mmol), N,N′-dimethylethylenediamine (8 μL, 0.066 mmol), potassium carbonate (61 mg, 0.44 mmol) in 5 mL dioxane in a sealed tube was stirred for 2 days at 120° C. The mixture was diluted with ethyl acetate (200 mL). It was washed with brine, dried, and concentrated in vacuo. The residue was treated with neat TFA for 15 min and directly subjected to prep HPLC to isolate the title compound. MS found for C18H17ClN6O2S (M+H)+ 417.1, 419.1 (Cl pattern).

Workup

washIt was washed with brine
customdried
concentrationconcentrated in vacuo
additionThe residue was treated with neat TFA for 15 min

Sources & evidence

ORD record: ord-24efe464cce349bbbc0a9f4a302544d9
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696352B2

Reaction notes

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