Trimethylamine → Trimethyl [3-[3-[3-(1-methyl-3-indolyl)-2,5-dioxo-3-pyrrolin-4-yl]-1-indolyl]propyl]ammonium methylsulphonate

HRID 345691Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:34])[NH:13][C:14](=[O:33])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH2:25][CH2:26][CH2:27][O:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:17]=2)=[CH:3]1.[CH3:35][N:36]([CH3:38])[CH3:37]>C(O)C>[CH3:32][S:29]([O-:31])(=[O:30])=[O:28].[CH3:35][N+:36]([CH3:38])([CH3:37])[CH2:27][CH2:26][CH2:25][N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([C:15]2[C:14](=[O:33])[NH:13][C:12](=[O:34])[C:11]=2[C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=2)=[CH:17]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 173 mg of the product of Example 58 and 2 ml of a 33% solution of trimethylamine in ethanol was heated at 90° C. for 3 hours. The solvent was evaporated and the residue was purified on silica gel with dichloromethane/methanol/acetic acid/water (60:18:2:3). Trituration with ethyl acetate gave 75 mg of trimethyl [3-[3-[3-(1-methyl-3-indolyl)-2,5-dioxo-3-pyrrolin-4-yl]-1-indolyl]propyl]ammonium methylsulphonate, m.p. 180°-185° C.

Workup

customThe solvent was evaporated
customthe residue was purified on silica gel with dichloromethane/methanol/acetic acid/water (60:18:2:3)

Sources & evidence

ORD record: ord-9ffd713f37984fb797011a4e8f7b9ce9
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05057614

Reaction notes

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