Potassium Hydroxide → HCID 59455123, compound

HRID 1401566Notes

Reaction equation

HRID 1401566 reaction equation
[CH3:1][N:2]1[CH2:25][CH2:24][C:5]2[N:6]([CH2:14][C:15]([C:18]3[CH:23]=[N:22][CH:21]=[CH:20][N:19]=3)(O)[CH3:16])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.S(Cl)(Cl)=O.[OH-].[K+]>C(Cl)Cl.O>[CH3:1][N:2]1[CH2:25][CH2:24][C:5]2[N:6](/[CH:14]=[C:15](/[C:18]3[CH:23]=[N:22][CH:21]=[CH:20][N:19]=3)\[CH3:16])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24386Thionyl ChlorideHCID 49779444HCID 49779444, compound

Product 1

HCID 59455123HCID 59455123, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)-2-(pyrazin-2-yl)propan-2-ol (336 mg, 1.0 mmol) in DCM (8 mL) was added at 0° C. a solution of thionyl chloride (594 mg, 5 mmol) in DCM (8 mL). The reaction mixture was stirred at RT for 30 min., volatiles were evaporated under reduced pressure and the residue was dissolved in N-methyl-2-pyrrolidone (4 mL). KOH (392 mg, 7.0 mmol) was added and the reaction mixture was stirred at RT for 5 min. and at 100° C. for 30 min. The reaction mixture was cooled to RT, diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure and the residue purified by HPLC. 1H NMR (CD3OD, TFA salt) δ (ppm): 9.0 (d, 1H), 8.70 (s, 1H), 8.60 (d, 1H), 7.70 (s, 1H), 7.38 (s, 1H), 7.15 (m, 2H), 4.78 (d, 1H), 4.40 (d, 1H), 3.90 (m, 1H), 3.60 (m, 1H), 3.25 (m, 2H), 3.20 (s, 3H), 2.50 (s, 3H), 2.10 (s, 3H).

Workup

  1. customvolatiles were evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in N-methyl-2-pyrrolidone (4 mL)
  3. stirringthe reaction mixture was stirred at RT for 5 min. and at 100° C. for 30 min
  4. temperatureThe reaction mixture was cooled to RT
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe residue purified by HPLC

Sources & evidence

ORD record
ord-5291686853de4ae4b3dcd1eecf52d322
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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