Triethylamine → HCID 59924923, compound

HRID 2300775Notes

Reaction equation

HRID 2300775 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:28]1([NH2:38])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1.C1COCC1>[C:28]1([NH:38][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:3])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 86401-NaphthylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69962054HCID 69962054, compound

Product 1

HCID 59924923HCID 59924923, compoundYield 18.7%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-[(S)-1-(3-carboxyphenyl)ethylamino]-4-[benzimidazol-1-yl]-pyrimidine (0.0376 mmol) and 1-naphthylamine (0.169 mmol) were mixed in CH2Cl2 (2 mL) and then triethylamine (0.187 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (0.172 mmol), and 4-dimethylaminopyridine (˜1 mg) were added in that order. Poor overall solubility was observed so THF (1 mL) was then added to the mixture, which became more homogeneous. The mixture was stirred at room temperature for 22 h then concentrated under reduced pressure. Purified by silica gel chromatography (1-2% MeOH in CH2Cl2) to yield 3.4 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.49 (br s, 1H); 8.41 (d, J=5.5 Hz, 1H); 8.17 (br s, 1H); 8.12 (br s, 1H); 8.02 (br s, 1H); 7.85-7.92 (m, 3H); 7.81 (m, 1H); 7.77 (d, J=8.2 Hz, 1H); 7.69 (d, J=7.5 Hz, 1H); 7.51-7.58 (m, 4H); 7.33 (br s, 2H); 6.82 (d, J=5.5 Hz, 1H); 5.78 (br s, 1H); 5.32 (br s, 1H); 1.71 (d, J=6.9 Hz, 3H). Mass Spectrum (ESI): m/e 485.2 (M+1).

Workup

  1. additionwas then added to the mixture, which
  2. concentrationthen concentrated under reduced pressure
  3. customPurified by silica gel chromatography (1-2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-0f586e8f99eb41fc87850ebcf3bddacd
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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