Tryptamine → HCID 9967347, compound

HRID 896287Notes

Reaction equation

HRID 896287 reaction equation
[OH:1][C:2]1[C:3]([C:12]([OH:14])=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH2:24][CH2:25][NH2:26])=[CH:16]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>CN(C=O)C>[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH2:24][CH2:25][NH:26][C:12]([C:3]2[C:2]([OH:1])=[C:11]3[C:6]([CH:7]=[CH:8][CH:9]=[N:10]3)=[CH:5][CH:4]=2)=[O:14])=[CH:16]1

Participants

7

Reactant 5

HCID 1150TryptamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2313638-Hydroxyquinoline-7-carboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 9967347HCID 9967347, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-hydroxyquinoline-7-carboxylic acid (0.23 g, 1.25 mmol), 2-(1H-Indol-3-yl)ethylamine (0.20 g, 1.25 mmol), 1-hydroxybenzotriazole (0.18 g, 1.37 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.26 g, 1.37 mmol), and triethylamine (0.7 mL, 4.99 mmol) in DMF (12 mL) was stirred at room temp overnight. The reaction mixture was concentrated under vacuum. The residue was dissolved in DMSO and subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provide the title compound as yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionThe residue was dissolved in DMSO
  3. customsubjected to HPLC purification on C-18 stationary phase
  4. washeluted with water/acetonitrile/TFA mobile phase
  5. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-c384d7839d58422184912a34466cf201
Source dataset
uspto-grants-2005_07
Patent number
US06919351B2

Reaction notes

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