HCID 49779381, compound → HCID 59455104, compound

HRID 1401573Notes

Reaction equation

HRID 1401573 reaction equation
[F:1][C:2]([F:29])([F:28])[CH2:3][N:4]1[CH2:27][CH2:26][C:7]2[N:8]([CH2:16][C:17]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)(O)[CH3:18])[C:9]3[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][C:14]=3[C:6]=2[CH2:5]1>S(Cl)(Cl)=O>[CH3:15][C:12]1[CH:11]=[CH:10][C:9]2[N:8](/[CH:16]=[C:17](/[C:20]3[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=3)\[CH3:18])[C:7]3[CH2:26][CH2:27][N:4]([CH2:3][C:2]([F:28])([F:29])[F:1])[CH2:5][C:6]=3[C:14]=2[CH:13]=1

Participants

3

Reactant 1

HCID 49779381HCID 49779381, compound

Product 1

HCID 59455104HCID 59455104, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

1-(2-(2,2,2-Trifluoroethyl)-1,2,3,4-tetrahydro-8-methylpyrido[4,3-b]indol-5-yl)-2-(pyridin-4-yl)propan-2-ol (200 mg, 0.4 mmol) was dissolved in thionyl chloride (2 mL), and stirred for 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: 195 mg. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.70 (d, 2H), 8.10 (d, 2H), 7.70 (s, 1H), 7.22 (s, 1H), 7.05 (m, 2H), 3.95 (s, 2H), 3.40 (m, 2H), 3.10 (m, 2H), 2.82 (m, 2H), 2.42 (s, 3H), 2.12 (s, 3H).

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-4704c6d3ea494099982469adb9922020
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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