HCID 49779378, compound → HCID 59455051, compound

HRID 1401592Notes

Reaction equation

HRID 1401592 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[CH2:26][N:25]([CH3:27])[CH2:24][CH2:23][C:9]=3[N:10]([CH2:13][C:14]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)(O)[CH3:15])[C:11]=2[CH:12]=1)([CH3:3])[CH3:2]>O=S(Cl)Cl>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[CH2:26][N:25]([CH3:27])[CH2:24][CH2:23][C:9]=3[N:10](/[CH:13]=[C:14](/[C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)\[CH3:15])[C:11]=2[CH:12]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 49779378HCID 49779378, compound

Product 1

HCID 59455051HCID 59455051, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

1-(7-Isopropyl-2-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-2-pyridin-4-yl-propan-2-ol (100 mg, 0.2 mmol) was dissolved in SOCl2 (1.0 mL) and stirred the reaction at RT for 2 h. After completion of starting material by monitoring TLC reaction mixture was concentrated under reduced pressure and saturated bicarbonate was added, extracted with EtOAc, organic layer was washed with water, dried over sodium sulfate and concentrated, and purified by reverse phase Chromatography. Yield: 68 mg. 1H NMR (DMSO-d6, oxalate salt) δ (ppm): 8.62 (d, 2H), 7.70 (d, 2H), 7.48 (s, 1H), 7.42 (d, 1H), 7.05 (m, 2H), 4.40 (m, 2H), 3.58 (m, 2H), 3.05 (m, 3H), 2.95 (s, 3H), 1.95 (s, 3H), 1.25 (d, 6H).

Workup

  1. customthe reaction at RT for 2 h
  2. customAfter completion of starting material by monitoring TLC reaction mixture
  3. concentrationwas concentrated under reduced pressure and saturated bicarbonate
  4. additionwas added
  5. extractionextracted with EtOAc, organic layer
  6. washwas washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. custompurified by reverse phase Chromatography

Sources & evidence

ORD record
ord-0aa353c473634db7a4ba79f3039185a0
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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