Hexamethylenetetramine → 6-Hydroxy-2-(4-isopropyl-piperazin-1-yl)-benzothiazole-7-carbaldehyde

HRID 579457Notes

Reaction equation

[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:32](O)=[O:33].C([O-])(O)=O.[Na+]>O>[OH:19][C:17]1[CH:16]=[CH:15][C:13]2[N:14]=[C:10]([N:7]3[CH2:6][CH2:5][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:9][CH2:8]3)[S:11][C:12]=2[C:18]=1[CH:32]=[O:33]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-(4-Isopropyl-piperazin-yl)-benzothiazol-6-ol (76 mg, 0.027 mmol), hexamethylenetetramine (153 mg, 1.10 mmol) and trifluoroacetic acid (2 mL) was stirred in a closed vessel under argon atmosphere at 120° C. for 1 h. The mixture was cooled to room temperature then 10 ml, of water was added. The pH of the mixture was adjusted to 8 by portionwise addition of saturated NaHCO3 solution, and extracted with dichloromethane (3×15 mL). After drying (MgSO4), filtration and evaporation of the solvent, the residue was purified by column chromatography (Kieselgel 60) using chloroform-methanol 49:1 as eluent followed by trituration with diethyl ether and n-hexane. The title compound (14 mg, 0.040 mmol, 14%) was obtained as a yellow solid.

Workup

temperatureThe mixture was cooled to room temperature
extractionextracted with dichloromethane (3×15 mL)
customAfter drying
filtration(MgSO4), filtration and evaporation of the solvent
customthe residue was purified by column chromatography (Kieselgel 60)

Sources & evidence

ORD record: ord-dfa51e4b6ae84106a5ae243ef81a7874
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040714B2

Reaction notes

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