Triethylamine → HCID 59924829, compound

HRID 2300779Notes

Reaction equation

HRID 2300779 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:2].O.[C:29]1(C)C=CC(S(O)(=O)=O)=C[CH:30]=1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>C(O)C.CN(C)C1C=CN=CC=1>[CH2:29]([O:2][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])[CH3:30]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69962054HCID 69962054, compound

Product 1

HCID 59924829HCID 59924829, compoundYield 333.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

2-[(S)-1-(3-carboxyphenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine (35.6 mg) was dissolved in ethanol (3 mL), then p-toluenesulfonic acid hydrate (˜1 mg) was added. The reaction was heated to 80° C. for 20 h after which no reaction progress was observed by thin layer chromatography. To this mixture was then added triethylamine (69 μL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (62 mg) and 4-dimethylaminopyridine (˜1 mg). Stirred at room temperature for 18 h. The mixture was concentrated under reduced pressure. This residue was purified first by silica gel column chromatography (98.5:1.5 CH2Cl2:MeOH) then on a 250 μM silica gel prep plate (1:1 hexanes:acetone) to yield 6.8 mg of the title compound. 1H NMR (500 MHz, CDCl3 partial): δ 8.49 (br s, 1H); 8.45 (d, J=5.4 Hz, 1H); 8.15 (s, 1H); 7.97 (m, 1H); 7.83 (d, J=8.0 Hz, 1H); 7.65 (d, J=7.8 Hz, 1H); 7.46 (t, J=7.7 Hz, 1H); 6.81 (d, J=5.5 Hz, 1H); 5.72 (br s, 1H); 5.27 (br s, 01H); 4.40 (q, J=7.2 Hz, 2H); 1.66 (d, J=7.1 Hz, 3H); 1.41 (t, J=7.2 Hz, 3H). Mass Spectrum (ESI): m/e 388.1 (M+1).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThis residue was purified first by silica gel column chromatography (98.5:1.5 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-4eae0d081fd646b8b5d0ff48a0eceea1
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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