Potassium Iodide → Nvp-abj688

HRID 1162994Notes

Reaction equation

HRID 1162994 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH2:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)[N:3]=1.[C-:34]#[N:35].[Na+].[I-].[K+]>CC(N(C)C)=O.O>[CH:11]1([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:2]([C:34]#[N:35])=[N:3][C:4]=3[NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH2:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 8929Sodium CyanideHCID 11784673(2-Chloro-9-cyclopentyl-purin-6-yl)-{2-[3-(4-methyl-piperazin-1-yl)-propoxy]-phenyl}-amine

Product 1

HCID 5288618Nvp-abj688

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
160 °C

Procedure

(2-Chloro-9-cyclopentyl-purin-6-yl)-{2-[3-(4-methyl-piperazin-1-yl)-propoxy]-phenyl}-amine (0.1 mmol), sodium cyanide (50 mg), potassium iodide (5 mg) are suspended in DMA (2 ml) and heated up to 160° C. and the mixture is stirred at this temperature for 24 hours. The mixture is diluted with water and extracted 3 times with ethyl acetate. The combined organic phases are washed with brine and the extract is dried over sodium sulfate and evaporated. The residue is dissolved in diethylether, filtered over powdered charcoal and cooled to 4° C. The solid material formed is filtered of and dried (vacuum). A white powder with mp. 136-138PC is obtained.

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. washThe combined organic phases are washed with brine
  3. dry with materialthe extract is dried over sodium sulfate
  4. customevaporated
  5. dissolutionThe residue is dissolved in diethylether
  6. filtrationfiltered over powdered charcoal
  7. temperaturecooled to 4° C
  8. customThe solid material formed
  9. filtrationis filtered of and
  10. customdried (vacuum)
  11. customA white powder with mp. 136-138PC is obtained

Sources & evidence

ORD record
ord-3d2b188d8c9f41e3951a81902372f26a
Source dataset
uspto-grants-2010_10
Patent number
US07820818B2

Reaction notes

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