HCID 49779380, compound → HCID 59455169, compound

HRID 1401574Notes

Reaction equation

HRID 1401574 reaction equation
[CH:1]1([N:4]2[CH2:27][CH2:26][C:7]3[N:8]([CH2:16][C:17]([C:20]4[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=4)(O)[CH3:18])[C:9]4[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][C:14]=4[C:6]=3[CH2:5]2)[CH2:3][CH2:2]1>S(Cl)(Cl)=O>[CH:1]1([N:4]2[CH2:27][CH2:26][C:7]3[N:8](/[CH:16]=[C:17](/[C:20]4[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=4)\[CH3:18])[C:9]4[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][C:14]=4[C:6]=3[CH2:5]2)[CH2:2][CH2:3]1

Participants

3

Reactant 1

HCID 49779380HCID 49779380, compound

Product 1

HCID 59455169HCID 59455169, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

1-(2-Cyclopropyl-1,2,3,4-tetrahydro-8-methylpyrido[4,3-b]indol-5-yl)-2-(pyridin-4-yl)propan-2-ol (100 mg, 0.27 mmol) was dissolved in thionyl chloride (1 mL), and stirred for 1-2 h at RT. The reaction mixture was concentrated under reduced pressure; the residue was cooled in ice water and basified with saturated aqueous NaHCO3. The product was extracted with EtOAc and organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by HPLC. Yield: 100 mg. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.80 (d, 2H), 8.30 (d, 2H), 7.78 (s, 1H), 7.38 (s, 1H), 7.18 (m, 2H), 4.70 (m, 2H), 3.90 (m, 2H), 3.22 (m, 2H), 3.15 (m, 1H), 2.45 (s, 3H), 2.16 (s, 3H), 1.20 (m, 2H), 1.10 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. temperaturethe residue was cooled in ice water
  3. extractionThe product was extracted with EtOAc and organic layer
  4. washwas washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-56218c6c807b4d49ac139d48e74d2d84
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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