5-Methoxytryptamine → HCID 54477526, compound

HRID 1872207Notes

Reaction equation

HRID 1872207 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:13][CH:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15](O)=[O:16])=[O:12])=[CH:5]2.Cl.CN(C)CCCN=C=NCC.[CH3:37][O:38][C:39]1[CH:50]=[C:49]2[C:42]([NH:43][CH:44]=[C:45]2[CH2:46][CH2:47][NH2:48])=[CH:41][CH:40]=1>CN(C)C=O>[CH3:37][O:38][C:39]1[CH:50]=[C:49]2[C:42](=[CH:41][CH:40]=1)[NH:43][CH:44]=[C:45]2[CH2:46][CH2:47][NH:48][C:15]([CH:14]([NH:13][C:11]([C:6]1[NH:7][C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2)=[O:12])[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16]

Participants

5

Reactant 3

HCID 18335-MethoxytryptamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21710786HCID 21710786, compound

Product 1

HCID 54477526HCID 54477526, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To 5.0 μmol of 2-[(5-fluoro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionic acid (50 μL of a 0.1 mM solution in dimethylformamide) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (50 μL of a 0.11 mM solution in DMF, 5.5 μmol) followed by 5-methoxytryptamine (50 μL of a 0.11 mM solution in DMF, 5.5 μmol). The reaction was agitated for 3 days and then concentated to dryness. The crude product was partitioned between chloroform (0.5 mL) and water (0.25 mL) and the organic layer was then concentrated to give the title compound. TSPMS ion (expected) 499 (499); HPLC RT 6.78 (25%).

Workup

  1. customThe crude product was partitioned between chloroform (0.5 mL) and water (0.25 mL)
  2. concentrationthe organic layer was then concentrated

Sources & evidence

ORD record
ord-9fd13be262f741fb9bc38f326c8b065c
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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