Sodium Bicarbonate → HCID 68944846, compound

HRID 41050Notes

Reaction equation

[CH3:1][N:2]([CH3:33])[CH2:3][CH2:4][N:5]1[C:29](=[O:30])[N:8]2[CH:9]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=3)[C:10]3[NH:11][C:12]4[C:17]([C:18]=3[CH2:19][C:7]2([CH3:31])[C:6]1=[O:32])=[CH:16][C:15]([O:20]C)=[CH:14][CH:13]=4.C(=O)(O)[O-].[Na+]>ClCCl>[NH3:2].[CH3:33][N:2]([CH3:1])[CH2:3][CH2:4][N:5]1[C:29](=[O:30])[N:8]2[CH:9]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=3)[C:10]3[NH:11][C:12]4[C:17]([C:18]=3[CH2:19][C:7]2([CH3:31])[C:6]1=[O:32])=[CH:16][C:15]([OH:20])=[CH:14][CH:13]=4

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 150 mg (3aSR,10RS)-2-(2-dimethylamino-ethyl)-10-(3-hydroxy-phenyl)-6-methoxy-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione (example 7) in 5 ml dichloromethane is cooled to −78° C. 20 ml bor tribromide are added drop wise. The suspension is stirred for 30 min at −78° C. and allowed to warm up to room temperature. After stirring for 1 h at room temperature, the mixture is cooled to 0° C. and an aqueous solution of sodium bicarbonate is added. The organic layer is separated and dried with magnesium sulfate. The solvent is removed at reduced pressure. After column chromatography (silica gel, ethyl acetate, methanol, ammonia 10:0.3:0.2), 49 mg of the title compound are obtained as a colourless foam. MS: m/z (MH+)=435.2

Workup

additionare added drop wise
temperatureto warm up to room temperature
stirringAfter stirring for 1 h at room temperature
temperaturethe mixture is cooled to 0° C.
customThe organic layer is separated
dry with materialdried with magnesium sulfate
customThe solvent is removed at reduced pressure

Sources & evidence

ORD record: ord-2549687f22224242b16c1914a8b0efe8
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530493B2

Reaction notes

Loading…