Potassium tert-butoxide → HCID 178480890, compound

HRID 222059Notes

Reaction equation

HRID 222059 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:14]3[CH2:15][CH2:16][C:17]4[C:18]5[C:23]([S:24][C:25]=4[C:13]=3[CH:12]=[N:11]2)=[N:22][CH:21]=[N:20][C:19]=5[O:26]CCC2C=CC([N+]([O-])=O)=CC=2)[CH2:4][CH2:3]1.CC(C)([O-])C.[K+]>C1COCC1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:14]3[CH2:15][CH2:16][C:17]4[C:18]5[C:19]([OH:26])=[N:20][CH:21]=[N:22][C:23]=5[S:24][C:25]=4[C:13]=3[CH:12]=[N:11]2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 67311978HCID 67311978, compound

Product 1

HCID 178480890HCID 178480890, compoundYield 114.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a yellow suspension of 3-[2-(4-methyl-piperazin-1-yl)-ethyl]-6-[2-(4-nitro-phenyl)-ethoxy]-4,5-dihydro-3H-10-thia-2,3,7,9-tetraaza-cyclopenta[a]fluorene (2.7 g, 5.2 mmol) in THF (125 ml) was added potassium tert-butoxide (0.92 g, 7.79 mmol) in one portion. The reaction mixture became a solution and then turned into a dark black solution. After stirring for 30 min, analytical HPLC showed no more starting material and two new major peaks. Solvents were evaporated and the dark residue was suspended in EtOAc. To above suspension was added 5 ml of 4M HCl and it turned into a light yellow suspension. The crude HCl salt of the desired product was collected by filtration, washed with EtOAc, and air-dried to afford the crude product (2.2 g, 104%). RT=0.41 min; [M+H]+=371.2.

Workup

  1. customSolvents were evaporated
  2. additionTo above suspension was added 5 ml of 4M HCl and it
  3. filtrationThe crude HCl salt of the desired product was collected by filtration
  4. washwashed with EtOAc
  5. customair-dried

Sources & evidence

ORD record
ord-7601d154690c4118a50c16fe91f13e33
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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