Water → Ammonia

HRID 41031Notes

Reaction equation

HRID 41031 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:27](=[O:28])[N:7]2[CH:8]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=3)[C:9]3[NH:10][C:11]4[C:16]([C:17]=3[CH2:18][C:6]2([CH3:29])[C:5]1=[O:30])=[CH:15][C:14]([Cl:19])=[CH:13][CH:12]=4.C(=O)([O-])[O-].[Na+].[Na+].[NH:37]1[CH2:40][CH2:39][CH2:38]1.O>C(#N)C>[NH3:4].[CH:39]([O:26][CH:22]([CH3:21])[CH3:23])([CH3:40])[CH3:38].[N:37]1([CH2:2][CH2:3][N:4]2[C:27](=[O:28])[N:7]3[CH:8]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=4)[C:9]4[NH:10][C:11]5[C:16]([C:17]=4[CH2:18][C:6]3([CH3:29])[C:5]2=[O:30])=[CH:15][C:14]([Cl:19])=[CH:13][CH:12]=5)[CH2:40][CH2:39][CH2:38]1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10422AzetidineHCID 68940637(3aSR,10RS)-2-(2-Bromo-ethyl)-6-chloro-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione

Product 3

HCID 222AmmoniaHCID 7914Diisopropyl EtherHCID 68943114(3aSR,10RS)-2-(2-Azetidin-1-yl-ethyl)-6-chloro-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 200 mg (3aSR,10RS)-2-(2-Bromo-ethyl)-6-chloro-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione (example 26) in 5 ml acetonitrile are added 87 mg sodium carbonate and 83 μl azetidine. The mixture is heated to reflux for 4 h. 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 10:0.2:0.1) and trituration with diisopropylether, 61 mg of the title compound are obtained as a colorless solid. MS: m/z (MH+)=465.1

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 4 h
  3. extractionthe mixture is extracted with ethyl acetate
  4. dry with materialThe organic layer is dried with magnesium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-6f2bf8e3e0144ac1944b28ff8dae6058
Source dataset
uspto-grants-2013_09
Patent number
US08530493B2

Reaction notes

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