Benzylamine → HCID 59924727, compound
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].[CH2:28]([NH2:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:28]([NH:35][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:2])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
2-[(S)-1-(3-carboxyphenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine (22.6 mg) and benzylamine (7.5 μL) were mixed in CH2Cl2 under nitrogen. Triethylamine (26 μL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (approx. 18 mg) and 4-dimethylaminopyridine (approx. 1 mg) were added and the mixture stirred at room temperature. After approximately 1.5 h another portion of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (13.5 mg) was added. One hour later the mixture was eluted directly on silica gel (95:5 CH2Cl2:MeOH) to yield 17.8 mg of the title compound. 1H NMR (500 MHz, CDCl3, partial): δ 8.46 (br s, 1H); 8.38 (d, J=5.2 Hz, 1H); 7.94 (s, 1H); 7.81 (d, J=7.7 Hz); 7.67 (m, 1H); 7.59 (d, J=7.8 Hz, 1H); 7.44 (t, J=7.7 Hz, 1H); 6.78 (d, J=5.5 Hz, 1H); 6.44 (s, 1H); 5.77 (br s, 1H); 5.24 (br s, 1H); 4.65 (m, 2H); 1.65 (d, J=6.8 Hz, 3H). Mass Spectrum (ESI): m/e 449.2 (M+1).
Workup
- washOne hour later the mixture was eluted directly on silica gel (95:5 CH2Cl2:MeOH)
Sources & evidence
- ORD record
- ord-a3ee5b675311474cb0af182338ead92a
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06498165B1
Reaction notes
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