Chlorosuccinimide → HCID 71558644, compound

HRID 1754568Notes

Reaction equation

HRID 1754568 reaction equation
N1C=CC=CC=1N1CC2C(=O)N(CC(F)(F)F)C3C=CC=CC=3C=2N1C1CCCCO1.[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38]1[CH:39]=[CH:40][C:41]2[C:42]3[C:43](=[CH:54][N:55](C4CCCCO4)[N:56]=3)[C:44](=[O:53])[N:45]([CH2:48][C:49]([F:52])([F:51])[F:50])[C:46]=2[CH:47]=1.[Cl:63]N1C(=O)CCC1=O>C(O)(=O)C.C(Cl)Cl>[Cl:63][C:39]1[C:38]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=2)=[CH:47][C:46]2[N:45]([CH2:48][C:49]([F:52])([F:51])[F:50])[C:44](=[O:53])[C:43]3[CH:54]=[N:55][NH:56][C:42]=3[C:41]=2[CH:40]=1

Participants

6

Reactant 3

HCID 31398ChlorosuccinimideHCID 86679791HCID 86679791, compoundHCID 86679812HCID 86679812, compound

Product 1

HCID 71558644HCID 71558644, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a suspension of 7-(pyrid-2-yl-1-(tetrahydro-2H-pyran-2-yl)-5-(2,2,2-trifluoroethyl)-2,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one and 7-(pyrid-2-yl)-2-(tetrahydro-2H-pyran-2-yl)-5-(2,2,2-trifluoroethyl)-2,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one [described in Step 1.5] (1.6 g, 3.73 mmol) in 32 mL of acetic acid is added N-chlorosuccinimide (2.49 g, 18.67 mmol). The reaction mixture is stirred for 3 hours at 80° C., cooled to room temperature and concentrated to dryness to give a yellow solid, which is dissolved in DCM. The solution is washed with saturated aqueous NaHCO3 solution and then with saturated aqueous NaCl solution, dried over Na2SO4, filtered and concentrated to give a yellow solid. The solid is taken up in DCM. After filtering off and drying, 542 mg of a white solid are obtained (yield: 35%).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated to dryness
  3. customto give a yellow solid, which
  4. washThe solution is washed with saturated aqueous NaHCO3 solution
  5. dry with materialwith saturated aqueous NaCl solution, dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow solid
  9. filtrationAfter filtering off
  10. customdrying

Sources & evidence

ORD record
ord-577be48eec9a49c99fd9516c50be02c8
Source dataset
uspto-grants-2015_10
Patent number
US09169246B2

Reaction notes

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