Ammonia → (3aSR,10RS)-2-(2-Amino-ethyl)-6-chloro-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione

HRID 41032Notes

Reaction equation

HRID 41032 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.[NH3:31]>CO>[NH2:31][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

Participants

4

Reactant 2

HCID 222AmmoniaHCID 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 1

HCID 68945183(3aSR,10RS)-2-(2-Amino-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 887MethanolSolvent2×

Conditions

Temperature
140 °C

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 3 ml methanol are added 1.2 ml of a 7 M solution of ammonia in methanol. The mixture is heated in a sealed tube to 140° C. for 1 h using a microwave reactor. The solvent is removed under reduced pressure. 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. The crude product is purified by preparative HPLC. 24 mg of the title compound are obtained. MS: m/z (MH+)=425.1

Workup

  1. customThe solvent is removed under reduced pressure
  2. additionWater is added
  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
  6. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-835a078bbfbe4c9ca385dd31a57d5a79
Source dataset
uspto-grants-2013_09
Patent number
US08530493B2

Reaction notes

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