Triethylamine → HCID 59924712, compound

HRID 2300781Notes

Reaction equation

HRID 2300781 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.[C:35]1([C@@H:41]([NH2:43])[CH3:42])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:35]1([C@@H:41]([NH:43][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])[CH3:42])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 758181-Phenethylamine, (-)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69962054HCID 69962054, compound

Product 1

HCID 59924712HCID 59924712, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-[(S)-1-(3-carboxyphenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine (15.5 mg) was dissolved in CH2Cl2 (2 mL), then triethylamine (30 μL) was added followed by (S)-1-phenylethylamine (17 μL), 1-(3-dimethylaminopropyl)-3-ethylcarbodimide hydrochloride (32.7 mg) and 4-dimethylaminopyridine (˜1 mg). The mixture was stirred at room temperature for 17 h then purified directly by silica gel column (60:40 hexanes:acetone) then on one 250 μm silica gel plate (90:10 CH2Cl2:MeOH) to yield 6.9 mg of the title compound. 1H NMR (500 MHz, CDCl3, partial): δ 8.48 (br s, 1H); 8.37 (d, J=5.5 Hz, 1H); 7.95 (s, 1H); 7.82 (d, J=7.5 Hz, 1H); 7.64 (d, J=7.8 Hz, 1H); 7.59 (d, J=7.5 Hz, 1H); 6.79 (d, J=5.5 Hz, 1H); 6.33 (d, J=7.8 Hz, 1H); 5.80 (br s, 1H); 5.36 (m, 1H); 5.24 (br s, 1H); 1.65 (d, J=6.9 Hz, 3H); 1.61 (d, J=6.9 Hz, 3H). Mass Spectrum (ESI): m/e 463.2 (M+1).

Workup

  1. customthen purified directly by silica gel column (60:40 hexanes:acetone)

Sources & evidence

ORD record
ord-57bc493b16f24f689ba735180b5a6f93
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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