Phenethylamine → HCID 59924823, compound

HRID 2300780Notes

Reaction equation

HRID 2300780 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C@@H:10]([NH:12][C:13]2[N:18]=[C:17]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]=[CH:20]3)[CH:16]=[CH:15][N:14]=2)[CH3:11])[CH:7]=[CH:8][CH:9]=1)([OH:3])=O.C([N:30]([CH2:33][CH3:34])[CH2:31]C)C.[CH2:35]([CH2:42]N)[C:36]1C=CC=[CH:38][CH:37]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:33]([N:30]([CH3:31])[C:1]([C:4]1[CH:5]=[C:6]([C@@H:10]([NH:12][C:13]2[N:18]=[C:17]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]=[CH:20]3)[CH:16]=[CH:15][N:14]=2)[CH3:11])[CH:7]=[CH:8][CH:9]=1)=[O:3])[C:34]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:42]=1

Participants

7

Reactant 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69962054HCID 69962054, compound

Product 1

HCID 59924823HCID 59924823, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-[(S)-1-(3-carboxyphenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine (32.7 mg) was dissolved in CH2Cl2 (2 mL), triethylamine (63 μL) added followed by N-benzylmethylamine (35 μL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (53 mg) and 4-dimethylaminopyridine (˜1 mg). Mixture was stirred at room temperature for 17 h then the solvent removed under reduced pressure. The residue was eluted on silica gel chromatography (1-2% MeOH in CH2Cl2) to yield 28.3 mg of the title compound. Mass Spectrum (ESI): m/e 463.2 (M+1).

Workup

  1. customthe solvent removed under reduced pressure
  2. washThe residue was eluted on silica gel chromatography (1-2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-62273e6a2cbe4062af3fda92f69950bd
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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