Serotonin → 3-(2-(2-(benzo[b]thiophen-3-yl)-9-isopropyl-9H-purin-6-ylamino)ethyl)-1H-indol-5-ol

HRID 1422504Notes

Reaction equation

HRID 1422504 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]2[N:14]=[C:13]3[C:9]([N:10]=[CH:11][N:12]3[CH:15]([CH3:17])[CH3:16])=[C:8](Cl)[N:7]=2)[C:3]2[CH:19]=[CH:20][CH:21]=[CH:22][C:2]1=2.[CH:23]1[C:28]([OH:29])=[CH:27][C:26]2[C:30]([CH2:33][CH2:34][NH2:35])=[CH:31][NH:32][C:25]=2[CH:24]=1>>[S:1]1[CH:5]=[C:4]([C:6]2[N:14]=[C:13]3[C:9]([N:10]=[CH:11][N:12]3[CH:15]([CH3:17])[CH3:16])=[C:8]([NH:35][CH2:34][CH2:33][C:30]3[C:26]4[C:25](=[CH:24][CH:23]=[C:28]([OH:29])[CH:27]=4)[NH:32][CH:31]=3)[N:7]=2)[C:3]2[CH:19]=[CH:20][CH:21]=[CH:22][C:2]1=2

Participants

3

Reactant 2

HCID 5202SerotoninHCID 594089202-(benzo[b]thiophen-3-yl)-6-chloro-9-isopropyl-9H-purine

Product 1

HCID 594089233-(2-(2-(benzo[b]thiophen-3-yl)-9-isopropyl-9H-purin-6-ylamino)ethyl)-1H-indol-5-ol

Procedure

Following the procedure of Example 15e, 2-(benzo[b]thiophen-3-yl)-6-chloro-9-isopropyl-9H-purine (b) (80 mg, 0.243 mmol) was reacted with serotonin. The reaction mixture was concentrated, then aqueous sodium bicarbonate solution was added. The mixture was extracted with ethyl acetate. The organic fractions were combined, dried over sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (0 to 5% MeOH in DCM eluant) to afford the title compound as an off-white solid. MS m/z 469.2 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionaqueous sodium bicarbonate solution was added
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (0 to 5% MeOH in DCM eluant)

Sources & evidence

ORD record
ord-507c6be4bec44b1d94a65881f79c3143
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

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