3-(4-(3-chloro-9-(benzenesulfonyl)-9H-pyrido[2,3-b]indol-6-yl)phenoxy)-N,N-diethylpropan-1-amine → 3-(4-(3-chloro-9H-pyrido[2,3-b]indol-6-yl)phenoxy)-N,N-diethylpropan-1-amine

HRID 341295Notes

Reaction equation

HRID 341295 reaction equation
[Cl:1][C:2]1[CH:38]=[N:37][C:5]2[N:6](S(C3C=CC=CC=3)(=O)=O)[C:7]3[C:12]([C:4]=2[CH:3]=1)=[CH:11][C:10]([C:13]1[CH:27]=[CH:26][C:16]([O:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[CH:15][CH:14]=1)=[CH:9][CH:8]=3>CO>[Cl:1][C:2]1[CH:38]=[N:37][C:5]2[NH:6][C:7]3[C:12]([C:4]=2[CH:3]=1)=[CH:11][C:10]([C:13]1[CH:27]=[CH:26][C:16]([O:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:22][CH3:23])[CH2:24][CH3:25])=[CH:15][CH:14]=1)=[CH:9][CH:8]=3

Participants

3

Reactant 1

HCID 461829693-(4-(3-chloro-9-(benzenesulfonyl)-9H-pyrido[2,3-b]indol-6-yl)phenoxy)-N,N-diethylpropan-1-amine

Product 1

HCID 461832043-(4-(3-chloro-9H-pyrido[2,3-b]indol-6-yl)phenoxy)-N,N-diethylpropan-1-amineYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(4-(3-chloro-9-(benzenesulfonyl)-9H-pyrido[2,3-b]indol-6-yl)phenoxy)-N,N-diethylpropan-1-amine (57 mg, 0.10 mmol) is added to a solution of Na° (23 mg, 1 mmol, 10 eq) in methanol (0.1 ml). The reaction is carried out at 65° C. for 2 hours, the mixture is then hydrolysed with ethanol and H2O and extracted with ethyl acetate (3×20 ml). The organic layers are dried over MgSO4, filtered, and concentrated under reduced pressure. The crude residue (orange solid) is purified over flash chromatography (eluted with THF/MeOH 9:1) to give the product R337 as a white solid (29 mg, 0.07 mmol) with a 70% yield. 1H NMR (CDCl3 300 MHz) δ ppm 8.42 (br s, 1H), 8.28 (br. s, 1H), 8.14 (br.s, 1H), 7.70 (dd, 1H, J=1.7, 8.5 Hz); 7.60-7.45 (m, 3H), 7.57 (d, 21-1, J=8.6 Hz), 7.01 (d, 21-1, J=8.7 Hz), 4.08 (t, 2H, J=6.3 Hz), 2.67 (t, 2H, J=7.3 Hz), 2.59 (q, 4H, J=7.1 Hz), 1.98 (p, 2H, J=6.8 Hz), 1.07 (t, 6H, J=7.1 Hz).

Workup

  1. extractionhydrolysed with ethanol and H2O and extracted with ethyl acetate (3×20 ml)
  2. dry with materialThe organic layers are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue (orange solid) is purified over flash chromatography (eluted with THF/MeOH 9:1)

Sources & evidence

ORD record
ord-b3b906d333ef4df3b80ce89831ed5924
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

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