HCID 49779378, compound → HCID 59455051, compound

HRID 1400531Notes

Reaction equation

HRID 1400531 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 the reaction was stirred at RT for 2 h. After completion of reaction (as monitored by TLC) reaction mixture was concentrated under vacuum and saturated bicarbonate solution was added. The desired compound was extracted with EtOAc, organic layer washed with water, dried over sodium sulfate and concentrated under vacuum. The crude compound was purified by reverse phase chromatography. Yield: 68 mg. 1H NMR (DMSO, 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, 2H).

Workup

  1. customAfter completion of reaction (as monitored by TLC) reaction mixture
  2. concentrationwas concentrated under vacuum and saturated bicarbonate solution
  3. additionwas added
  4. extractionThe desired compound was extracted with EtOAc, organic layer
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe crude compound was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-fe642570f8034f40bcb595aa2aa011fc
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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