Triethylamine → HCID 59924876, compound

HRID 2300783Notes

Reaction equation

HRID 2300783 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(N(CC)CC)C.[NH2:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[NH:41][CH:40]=[CH:39]2.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[NH:41]1[C:42]2[C:38](=[CH:37][C:36]([NH:35][C:1]([C:4]3[CH:5]=[C:6]([C@@H:10]([NH:12][C:13]4[N:18]=[C:17]([N:19]5[C:23]6[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=6[N:21]=[CH:20]5)[CH:16]=[CH:15][N:14]=4)[CH3:11])[CH:7]=[CH:8][CH:9]=3)=[O:2])=[CH:44][CH:43]=2)[CH:39]=[CH:40]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 788675-AminoindoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69962054HCID 69962054, compound

Product 1

HCID 59924876HCID 59924876, compoundYield 14.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-[(S)-1-(3-carboxyphenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine (19.2 mg) was dissolved in CH2Cl2 (2 mL), then triethylamine (37 μL) was added followed by 5-aminoindole (19.0 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (27.3 mg) and 4-dimethylaminopyridine (˜1 mg). The mixture was stirred at room temperature for 30 min then eluted on silica gel column (2-4%MeOH in CH2Cl2) then on one 250 μm silica gel plate (1:1 hexanes:acetone) to yield 3.7 mg of the title compound. 1H NMR (500 MHz, CDCl3,partial): δ 8.50 (br s, 1H); 8.40 (d, J=5.5 Hz, 1H); 8.22 (br s, 1H); 8.03 (s, 1H); 7.96 (br s, 1H); 7.87 (s, 1H); 7.64 (d, J=7.8 Hz, 1H); 7.51 (t, J=7.8 Hz, 1H); 7.25 (m, 1H); 6.81 (d, J=5.5 Hz, 1H); 6.56 (br s, 1H); 5.89 (br s, 1H); 5.29 (br s, 1H); 1.69 (d, J=6.9 Hz, 3H). Mass Spectrum (ESI): m/e 474.3 (M+1).

Workup

  1. washthen eluted on silica gel column (2-4%MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-abe14e16eb104a0cb6baf68b5c4ea233
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

Loading…