Phenethylamine → HCID 59924721, compound

HRID 2300778Notes

Reaction equation

HRID 2300778 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)(O)=[O:2].C(Cl)Cl.[CH2:31]([NH2:39])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[C:33]1([CH2:32][CH2:31][NH:39][C:1]([C:4]2[CH:5]=[C:6]([C@@H:10]([NH:12][C:13]3[N:18]=[C:17]([N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[N:21]=[CH:20]4)[CH:16]=[CH:15][N:14]=3)[CH3:11])[CH:7]=[CH:8][CH:9]=2)=[O:2])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 1001PhenethylamineHCID 6344DichloromethaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69962054HCID 69962054, compound

Product 1

HCID 59924721HCID 59924721, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Procedure

Made in the same manner as EXAMPLE 62 using 2-[(S)-1-(3-carboxyphenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine (37.2 mg), CH2Cl2 (2 mL), triethylamine (72 μL), phenethylamine (39 μL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (58 mg) and 4-dimethylaminopyridine (˜1 mg). Run for 18 h then concentrated under reduced pressure and purified by silica gel chromatography (98:2 CH2Cl2:MeOH) to yield 21.6 mg of the title compound. 1H NMR (500 MHz, CDCl3 partial): δ 8.48 (br s, 1H); 8.40 (d, J=5.5 Hz, 1H); 7.84 (m, 2H); 7.56 (m, 2H); 7.42 (t, J=7.7 Hz, 1H); 6.80 (d, J=5.5 Hz,1H); 6.10 )br s, 1H); 5.69 (br s, 1H); 5.23 (br s, 1H); 3.72 (m, 2H); 2.94 (t, J=7.0 Hz, 2H); 1.65 (d, J=6.9 Hz, 3H). Mass Spectrum (ESI): m/e 463.2 (M+1).

Workup

  1. concentrationthen concentrated under reduced pressure
  2. custompurified by silica gel chromatography (98:2 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-45983ab016e640f0be15f16f1f56cc25
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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