Tryptamine → HCID 86643466, compound

HRID 1422491Notes

Reaction equation

HRID 1422491 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[C:4](Cl)[N:3]=1.[NH2:18][CH2:19][CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1>CC(O)C>[NH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21]([CH2:20][CH2:19][NH:18][C:4]2[N:3]=[C:2]([Cl:1])[N:10]=[C:9]3[C:5]=2[N:6]=[CH:7][N:8]3[CH:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:22]1

Participants

4

Reactant 2

HCID 1150TryptamineHCID 86643465HCID 86643465, compound

Product 1

HCID 86643466HCID 86643466, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of methyl 2-(2,6-dichloro-9H-purin-9-yl)propanoate (b) (600 mg, 2.2 mmol), tryptamine (420 mg, 2.6 mmol) and 2-propanol (30 mL) was heated at 85° C. in a sealed tube for 16 h. The reaction mixture was cooled to room temperature and concentrated. The residue was purified by silica gel chromatography (10 to 80% ethyl acetate in hexane eluant) to afford the title compound as a white solid. MS m/z 360.1 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography (10 to 80% ethyl acetate in hexane eluant)

Sources & evidence

ORD record
ord-c42f18ead6df46f1b33c99c73b21dcf7
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

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