Triethylamine → HCID 59924681, compound

HRID 2300782Notes

Reaction equation

HRID 2300782 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][CH2:36][C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[N:40]1[CH:41]=[CH:42][C:37]([CH2:36][NH:35][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:39]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 773174-PyridinemethanamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69962054HCID 69962054, compound

Product 1

HCID 59924681HCID 59924681, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-[(S)-1-(3-carboxyphenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine (15.4 mg) was dissolved in CH2Cl2 (2 mL), then triethylamine (30 μL) was added followed by 4-aminomethylpyridine (14 μL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (26.8 mg) and 4-dimethylaminopyridine (˜1 mg). The mixture was stirred at room temperature for 19 h then eluted directly on silica gel column (2-10%MeOH in CH2Cl2) to yield 8.9 mg of the title compound. 1H NMR (500 MHz, CDCl3,partial): δ 8.56 (m, 2H); 8.46 (br s, 1H); 8.39 (d, J=5.5 Hz, 1H); 7.96 (s, 1H); 7.81 (d, J=7.9 Hz, 1H); 7.71 (d, J=7.8 Hz, 1H); 7.63 (d, J=7.8 Hz, 1H); 7.47 (t, J=7.7 Hz, 1H); 7.24 (d, J=5.9 Hz, 1H); 6.79 (d, J=5.5 Hz, 1H); 6.64 (br s, 1H); 5.77 (br s, 1H); 5.5.24 (br s, 1H); 4.65 (m, 2H); 1.66 (d, J=7.1 Hz, 3H). Mass Spectrum (ESI): m/e 450.2 (M+1).

Workup

  1. washthen eluted directly on silica gel column (2-10%MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-d837c09868364f07ac4b91afd4f823fd
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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