Ethylamine → HCID 59924860, compound

HRID 2300776Notes

Reaction equation

HRID 2300776 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.[CH2:28]([N:30](CC)CC)[CH3:29].C(N)C.Cl.CN(C)CCCN=C=NCC>C1COCC1.CN(C)C1C=CN=CC=1>[CH2:28]([NH:30][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])[CH3:29]

Participants

7

Reactant 4

HCID 6341Ethylamine2×HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 69962054HCID 69962054, compound

Product 1

HCID 59924860HCID 59924860, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

2-[(S)-1-(3-carboxyphenyl)ethylamino]-4-[benzimidazol-1-yl]-pyrimidine (27.4 mg) was dissolved in THF (1 mL), and triethylamine (53 μL) was added. A solution of 2.0M ethylamine in THF (76 μL) was added followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (26.9 mg) and 4-dimethylaminopyridine (˜1 mg). Stirred at room temperature for 2 h then another portion of 2.0M ethylamine in THF (76 μL) was added along with more 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (27.4 mg). 1.5 h later the mixture was concentrated under reduced pressure then purified by silica gel chromatography (98:2 CH2Cl2:MeOH) to yield 18.2 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.48 (br s, 1H); 8.39 (d, J=5.5 Hz, 1H); 7.90 (m, 1H); 7.82 (d, J=7.5 Hz, 1H); 7.64 (m, 1H); 7.58 (d, J=5.8 Hz, 1H); 7.44 (t, J=7.7 Hz, 1H); 7.34 (m, 3H); 6.79 (d, J=5.5 Hz, 1H); 6.11 (br s, 1H); 5.81 (br s, 1H); 5.25 (br s, 1H); 3.49 (m, 2H); 1.65 (d, J=6.9 Hz, 3H); 1.25 (t, J=7.3 Hz, 3H). Mass Spectrum (ESI): m/e 387.1 (M+1).

Workup

  1. concentration1.5 h later the mixture was concentrated under reduced pressure
  2. customthen purified by silica gel chromatography (98:2 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-43477f8aa6fc4d33b4f8561bc6711c81
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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