Water → Ammonia

HRID 41030Notes

Reaction equation

Br[CH2:2][CH2:3][N:4]1[C:28](=[O:29])[N:7]2[CH:8]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=3)[C:9]3[NH:10][C:11]4[C:16]([C:17]=3[CH2:18][C:6]2([CH3:30])[C:5]1=[O:31])=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=4.[C:32](=O)([O-])[O-].[Na+].[Na+].CN.O.[C:41](#[N:43])[CH3:42]>O1CCCC1>[NH3:4].[CH:14]([O:19][CH:41]([CH3:42])[CH3:32])([CH3:15])[CH3:13].[OH:27][C:23]1[CH:22]=[C:21]([CH:8]2[C:9]3[NH:10][C:11]4[C:16](=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=4)[C:17]=3[CH2:18][C:6]3([CH3:30])[C:5](=[O:31])[N:4]([CH2:3][CH2:2][NH:43][CH3:41])[C:28](=[O:29])[N:7]23)[CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 150 mg (3aSR,10RS)-2-(2-Bromo-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 24) in 5 ml acetonitrile are added 66 mg sodium carbonate and 920 μl of a 2 M solution of methyl amine in tetrahydrofurane. The mixture is heated in a sealed tube to 140° C. for 3 h using a microwave reactor. Water is added and the mixture is extracted with ethyl acetate. The organic layer is dried with magnesium sulfate. The solvent is removed under reduced pressure. After column chromatography (silica gel; ethyl acetate, methanol, ammonia 10:1:0.5) and trituration with diisopropylether, 60 mg of the title compound are obtained as a colorless solid. MS: m/z (MH+)=435.1

Workup

extractionthe mixture is extracted with ethyl acetate
dry with materialThe organic layer is dried with magnesium sulfate
customThe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-3432da1bd2764eeba9be487c123b8bdf
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530493B2

Reaction notes

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