Hydrochloric Acid → HCID 66998714, compound

HRID 559224Notes

Reaction equation

HRID 559224 reaction equation
[Cl:1][CH2:2][C:3]1[N:7]([CH3:8])[N:6]=[C:5]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13]2[N:19]([CH3:32])[C:20](=[O:31])[C:21]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=4[Cl:30])=[CH:22][C:12]3=2)[CH:4]=1.C([O-])([O-])=O.[K+].[K+].[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.Cl>CN(C=O)C.CCOC(C)=O.O>[ClH:1].[Cl:30][C:24]1[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:23]=1[C:21]1[C:20](=[O:31])[N:19]([CH3:32])[C:13]2[N:14]([CH3:18])[C:15]3[C:11]([C:12]=2[CH:22]=1)=[CH:10][C:9]([C:5]1[CH:4]=[C:3]([CH2:2][N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)[N:7]([CH3:8])[N:6]=1)=[CH:17][CH:16]=3

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 66997926HCID 66997926, compound

Product 1

HCID 66998714HCID 66998714, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

100 mg (0.2 mmol) of compound A, 6-(5-chloromethyl-1-methyl-1H-pyrazol-3-yl)-3-(2,4-dichlorophenyl)-1,9-dimethyl-1,9-dihydropyrido[2,3-b]indol-2-one are dissolved in 5 ml of anhydrous DMF. 55 mg (0.4 mmol) of K2CO3 and 22 μl (0.25 mmol) of morpholine are added. The mixture is heated at 80° C. overnight. It is allowed to return to ambient temperature and poured into water. The mixture is extracted with EtOAc. The organic phase is washed with a saturated NaCl solution. It is dried over Na2SO4, filtered and evaporated to dryness. Purification is carried out on a silica column, elution being carried out with a 95/05 EtOAc/MeOH mixture. The product obtained is dissolved in EtOAc and 0.5 ml of a saturated solution of HCl in Et2O/petroleum ether is added. The precipitate formed is filtered off and washed with ether. The product is taken up in MeOH and evaporated to dryness.

Workup

  1. customto return to ambient temperature
  2. extractionThe mixture is extracted with EtOAc
  3. washThe organic phase is washed with a saturated NaCl solution
  4. dry with materialIt is dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customPurification
  8. washis carried out on a silica column, elution
  9. customThe product obtained
  10. customThe precipitate formed
  11. filtrationis filtered off
  12. washwashed with ether
  13. customevaporated to dryness

Sources & evidence

ORD record
ord-bafe2c7f30384503a3960d191853f414
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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