Dimethylformamide → HCID 16070336, compound

HRID 1710708Notes

Reaction equation

HRID 1710708 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[C:13]([NH2:15])[CH:12]=[N:11][C:10]=1[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.[CH3:22][N:23](C)[CH:24]=[O:25]>>[CH:22]1([NH:23][C:24]([NH:15][C:13]2[CH:12]=[N:11][C:10]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=3)[N:14]=2)=[O:25])[CH2:6][CH2:5][CH2:4][CH2:9]1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 16071664HCID 16071664, compound

Product 1

HCID 16070336HCID 16070336, compoundYield 41%

Conditions

Temperature
70 °C

Procedure

Sodium hydride (17 mg, 0.43 mmol) in anhydrous dimethylformamide (3.5 mL) was stirred at 0° C. under nitrogen atmosphere. 6-Pyridin-2-yl-5-pyridin-4-ylpyrazin-2-amine (Example 12, 90 mg, 0.36 mmol) in anhydrous dimethylformamide (2.5 mL) and cyclopentylisocianate (50 μL, 0.43 mmol) were sequentially added. The mixture was stirred at 70° C. under nitrogen atmosphere for 1 h 30 min. Dimethylformamide was removed in vacuo and the resulting solid was triturated with hexanes-dichloromethane, filtered, washed with hexanes and dried. Silica gel flash chromatography of the solid (dichloromethane to dichloromethane/methanol 95:5) afforded the title compound (53 mg, 41%) as a white solid.

Workup

  1. customDimethylformamide was removed in vacuo
  2. customthe resulting solid was triturated with hexanes-dichloromethane
  3. filtrationfiltered
  4. washwashed with hexanes
  5. customdried

Sources & evidence

ORD record
ord-53b1950d454c4db6b394c623d76b2710
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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