1,3-Propanediamine, N1,N1,N3-trimethyl- → HCID 54143483, compound

HRID 651097Notes

Reaction equation

HRID 651097 reaction equation
[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][NH:6][CH3:7].[Cl:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([C:19]([NH:21][CH:22]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:23]([OH:25])=O)=[O:20])=[CH:13]2>>[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][N:6]([CH3:7])[C:23]([CH:22]([NH:21][C:19]([C:14]1[NH:15][C:16]2[C:12]([CH:13]=1)=[CH:11][C:10]([Cl:9])=[CH:18][CH:17]=2)=[O:20])[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:25]

Participants

3

Reactant 2

HCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 155210162-[(5-Chloro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionic acid

Product 1

HCID 54143483HCID 54143483, compound

Procedure

N,N,N′-Trimethyl-1,3-diaminopropane (0.31 mmol) and 2-[(5-chloro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionic acid (0.28 mmol) were coupled according to Procedure A (0-25° C. reaction temperature, 120 hour reaction time) and the product purified by chromatography on silica gel eluted with 1-8% ethanol in dichloromethane containing 0.5% ammonium hydroxide: Yield 86 mg, 69%; HPLC (40/60) 7.57 minutes (>99%); mp 187-190.5° C.; TSPMS 441/443 (MH+, 100%);

Workup

  1. customthe product purified by chromatography on silica gel
  2. washeluted with 1-8% ethanol in dichloromethane containing 0.5% ammonium hydroxide
  3. customHPLC (40/60) 7.57 minutes (>99%)

Sources & evidence

ORD record
ord-f41d9d78ee9e447b82ea6bd32f7c501a
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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