3,4-Dichloro-1,2,5-thiadiazole → 4-(4-Chloro-[1,2,5]thiadiazol-3-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 907540Notes

Reaction equation

[N:1]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:15][C:16]1[C:20](Cl)=[N:19][S:18][N:17]=1>CN(C=O)C>[C:11]([O:10][C:8]([N:1]1[CH2:7][CH2:6][CH2:5][N:4]([C:20]2[C:16]([Cl:15])=[N:17][S:18][N:19]=2)[CH2:3][CH2:2]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of t-butyl 1-homopiperazine carboxylate (45 mmol, 9 g) and DMF (50 ml) was heated to 100° C. 3,4-dichloro-1,2,5-thiadiazole (23 mmol, 2.2 ml) was added to the mixture and stirred at 100° C. for 2 days. The mixture was quenched with ice/water and extracted with ethyl acetate (3×). The combined organic layer was washed with water (2×) and brine, dried over sodium sulfate, filtered and concentrated. The crude was purified on silica column using 20% ethyl acetate/hexanes to give 5.8 g of product.

Workup

customThe mixture was quenched with ice/water
extractionextracted with ethyl acetate (3×)
washThe combined organic layer was washed with water (2×) and brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude was purified on silica column

Sources & evidence

ORD record: ord-d803f609959c4183888beaf29cc87194
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013156B2

Reaction notes

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