Methyl isothiocyanate → 2,2-Dimethylpropyl 4-{4-[5-(methylamino)-1,2,4-thiadiazol-3-yl]pyridin-2-yl}-1-piperazinecarboxylate

HRID 421830Notes

Reaction equation

[NH2:1][C:2](=[N:23]O)[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:16])[CH2:11][CH2:10]2)[CH:4]=1.[CH3:25][N:26]=[C:27]=[S:28]>CN(C)C=O.C(OCC)(=O)C>[CH3:25][NH:26][C:27]1[S:28][N:23]=[C:2]([C:3]2[CH:8]=[CH:7][N:6]=[C:5]([N:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:16])[CH2:11][CH2:10]3)[CH:4]=2)[N:1]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2,2-Dimethylpropyl 4-{4-[amino(hydroxyimino)methyl]pyridin-2-yl}piperazine-1-carboxylate (122 mg) obtained in Example 26-1) was dissolved in dimethylformamide (1 mL), and methyl isothiocyanate (41 mg) was added thereto and stirred at 100° C. for 1 hour. The reaction liquid was diluted with ethyl acetate, washed with water and saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was isolated and purified through thin-layer silica gel chromatography (hexane/ethyl acetate=1/1) to obtain 31.3 mg of the entitled compound as a colorless solid.

Workup

customThe reaction liquid
washwashed with water and saturated saline water
dry with materialdried with anhydrous sodium sulfate
customThe solvent was evaporated away
customthe resulting residue was isolated
custompurified through thin-layer silica gel chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record: ord-7164f330eac746529dd315db99bb8778
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101618B2

Reaction notes

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