2-Amino-2-methyl-1-propanol → 2-{[3-(4-Bromophenyl)-1,2,4-thiadiazol-5-yl]amino}-2-methylpropan-1-ol

HRID 1436444Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11](Cl)[S:10][N:9]=2)=[CH:4][CH:3]=1.[NH2:14][C:15]([CH3:19])([CH3:18])[CH2:16][OH:17]>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([NH:14][C:15]([CH3:19])([CH3:18])[CH2:16][OH:17])[S:10][N:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 125 °C

Procedure

3-(4-Bromophenyl)-5-chloro-1,2,4-thiadiazole (2.0 g, 7.3 mmol), prepared in the previous step, was dissolved in 2-amino-2-methylpropanol and heated to 125° C. for 16 h. The mixture was cooled, diluted with ethyl acetate, washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (10% acetone in hexane) afforded 2-{[3-(4-bromophenyl)-1,2,4-thiadiazol-5-yl]amino}-2-methylpropan-1-ol (0.85 g, 35%) as a pale yellow solid. HRMS: calcd for C12H14BrN3OS+H+, 328.01137; found (ESI, [M+H]+), 328.0113; Analytical HPLC: purity 100% at 210-370 nm, 10.0 min; 100% at 252 nm, 10.0 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH 3.5/ACN+MeOH) for 10 min, hold 4 min.

Workup

temperatureThe mixture was cooled
washwashed with water, brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-d24a7fe9878a42ef97be53eb71926b30
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618990B2

Reaction notes

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