Potassium Hydroxide → HCID 59455036, compound

HRID 1400530Notes

Reaction equation

HRID 1400530 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]([C:15]3[CH:20]=[N:19][CH:18]=[CH:17][N:16]=3)(O)[CH3:13])[C:6]3[CH2:21][CH2:22][N:23]([CH3:25])[CH2:24][C:5]=3[C:4]=2[CH:3]=1.S(Cl)(Cl)=O.[OH-].[K+]>C(Cl)Cl.CN(C=O)C.CN1C(=O)CCC1.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7](/[CH:11]=[C:12](/[C:15]3[CH:20]=[N:19][CH:18]=[CH:17][N:16]=3)\[CH3:13])[C:6]3[CH2:21][CH2:22][N:23]([CH3:25])[CH2:24][C:5]=3[C:4]=2[CH:3]=1

Participants

8

Reactant 3

HCID 14797Potassium HydroxideHCID 24386Thionyl ChlorideHCID 49779445HCID 49779445, compound

Product 1

HCID 59455036HCID 59455036, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 1-(8-chloro-2-methyl 1,2,3,4 tetrahydro-pyrido(4,3-b)indol-5-yl)-2-pyrazin-2-yl-propan-2-ol (500 mg, 1.4 mmol) in DCM (8 mL) and DMF (2 drops) was stirred at 0-10° C. Thionyl chloride (0.5 mL, 7.0 mmol) diluted in DCM (8 mL) was added to the reaction mixture, which was stirred at RT for 1 h. The solvent was removed under vacuum to obtain the crude foamy solid. The solid was dissolved in NMP (6 mL) and the reaction mixture stirred for 5 min. Powdered KOH (551 mg, 9.83 mmol) was added to the reaction mixture and the mixture heated at 100° C. for 30 min. After completion of reaction, the reaction mixture was poured in water and extracted with EtOAc (100 mL×3). The organic layer was washed with water, concentrated under vacuum to obtain the crude product which was purified by reverse phase HPLC. 1H NMR (CDCl3, free base) δ (ppm): 8.80 (s, 1H), 8.58 (d, 1H), 8.50 (d, 1H), 7.62 (s, 1H), 7.40 (s, 1H), 7.15 (d, 1H), 7.05 (d, 1H), 3.70 (s, 2H), 2.82 (m, 4H), 2.58 (s, 3H), 2.10 (s, 3H).

Workup

  1. additionwas added to the reaction mixture, which
  2. customThe solvent was removed under vacuum
  3. customto obtain the crude foamy solid
  4. stirringthe reaction mixture stirred for 5 min
  5. temperaturethe mixture heated at 100° C. for 30 min
  6. customAfter completion of reaction
  7. extractionextracted with EtOAc (100 mL×3)
  8. washThe organic layer was washed with water
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-becad21937a14f9287732568d0d3e5a7
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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