Dimethylformamide → HCID 178478337, compound

HRID 1678758Notes

Reaction equation

HRID 1678758 reaction equation
[C:1]1([C:7]2[C:8]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:30][CH2:29][CH:28]([C:31]5[N:35]=[C:34]([C:36]6[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=6)[NH:33][N:32]=5)[CH2:27][CH2:26]4)=[CH:20][CH:19]=3)=[N:9][C:10]3[CH:11]=[CH:12][NH:13][C:14](=O)[C:15]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:44].CN(C=O)C.C([O-])(O)=O.[Na+]>O>[Cl:44][C:14]1[N:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH:16]=[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([C:18]1[CH:19]=[CH:20][C:21]([CH2:24][N:25]3[CH2:26][CH2:27][CH:28]([C:31]4[NH:35][C:34]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=5)=[N:33][N:32]=4)[CH2:29][CH2:30]3)=[CH:22][CH:23]=1)=[N:9]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178518688Akt1 and Akt2-IN-1

Product 1

HCID 178478337HCID 178478337, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 8-7 (5.5 g, 10.2 mmol) and POCl3 (50.0 g, 326.1 mmol) and DMF (0.3 g, 4.1 mmol) was heated to reflux at 130° C. for 3 hr. The reaction mixture was cooled and concentrated to remove POCl3. 40 mL Toluene was added and concentrated to obtain a solid. To the solid was added 50 mL H2O and 40 mL NaHCO3 (saturated) and 20 mL 1NNaOH to pH=9. The mixture was stirred to precipitate a solid which was collected via filtration as the desired product 8-8. It was washed by water and CH3CN and dried under vacuum.

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated
  4. customto remove POCl3
  5. addition40 mL Toluene was added
  6. concentrationconcentrated
  7. customto obtain a solid
  8. customto precipitate a solid which
  9. filtrationwas collected via filtration as the desired product 8-8
  10. washIt was washed by water and CH3CN
  11. customdried under vacuum

Sources & evidence

ORD record
ord-6c502adf1d5a475885df52b064ddca4e
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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