N,N-bis(3-aminopropyl)methylamine → HCID 67392430, compound

HRID 908667Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([CH3:10])[CH2:6][CH2:7][CH2:8][NH2:9].CO[C:13]1[C:29](=[O:30])[C:17]2[N:18]=[C:19]([C:21]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[O:22])[S:20][C:16]=2[C:15](=[O:31])[CH:14]=1>C(O)C>[CH3:10][N:5]([CH2:6][CH2:7][CH2:8][NH:9][C:13]1[C:29](=[O:30])[C:17]2[N:18]=[C:19]([C:21]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[O:22])[S:20][C:16]=2[C:15](=[O:31])[CH:14]=1)[CH2:4][CH2:3][CH2:2][NH:1][C:13]1[C:29](=[O:30])[C:17]2[N:18]=[C:19]([C:21]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[O:22])[S:20][C:16]=2[C:15](=[O:31])[CH:14]=1

Participants

Conditions

Temperature: 85 °C

Procedure

51 μl (0.32 mmol; 0.5 equivalent) of N-(3-aminopropyl)-N-methylpropane-1,3-diamine is added to 200 mg (0.65 mmol) of 5-methoxy-2-(morpholin-4-ylcarbonyl)-1,3-benzothiazole-4,7-dione in solution in 15 ml of ethanol. The reaction mixture is maintained under stirring at 85° C. for 2 hours, then the solvent is evaporated off under reduced pressure and the expected product is purified by chromatography on a silica column (eluent: dichloromethane/methanol mixture 95/5) then recrystallized from a mixture of acetone and ethyl ether and 110 mg (yield=24%) of 5.5′-[(methylimino)bis(propane-3,1-diylimino)]bis[2-(morpholin-4-ylcarbonyl)-1,3-benzothiazole-4,7-dione] is obtained in the form of a red powder. Melting point=207-208° C.

Workup

temperatureThe reaction mixture is maintained
customthe solvent is evaporated off under reduced pressure
customthe expected product is purified by chromatography on a silica column (eluent: dichloromethane/methanol mixture 95/5)
customthen recrystallized from a mixture of acetone and ethyl ether

Sources & evidence

ORD record: ord-8058d8ee470d4576ab8bfa5c5146b306
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017637B2

Reaction notes

Loading…