Dimethylformamide → HCID 86640964, compound

HRID 906409Notes

Reaction equation

HRID 906409 reaction equation
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH2:18][CH2:19][CH2:20][Cl:21])[CH:11]=[CH:10]2.CN([CH:25]=[O:26])C>>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH2:18][CH2:19][CH2:20][Cl:21])[CH:11]=[C:10]2[CH:25]=[O:26]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 57439896HCID 57439896, compound

Product 1

HCID 86640964HCID 86640964, compound

Conditions

Temperature
0 °C

Procedure

Phosphorousoxychloride (2.37 mL) was added dropwise to DMF (10 mL) stirring at 0° C. The resulting mixture was warmed to room temperature over 2 h before being treated with a solution of 6-bromo-2-(3-chloropropyl)isoquinolin-1(2H)-one (Example 10a, 0.85 g) in DMF (10 mL). The resulting solution was heated at 80° C. for 10 h. The cooled reaction was quenched with iced water and extracted with ethyl acetate. The organics were washed with brine, dried (MgSO4) and concentrated in vacuo to give the subtitle compound (0.91 g).

Workup

  1. temperatureThe resulting mixture was warmed to room temperature over 2 h
  2. temperatureThe resulting solution was heated at 80° C. for 10 h
  3. customThe cooled reaction
  4. customwas quenched with iced water
  5. extractionextracted with ethyl acetate
  6. washThe organics were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1370dcfa7fc3484aa19b028f976cd82d
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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