P-Anisidine → HCID 59924908, compound

HRID 2300785Notes

Reaction equation

HRID 2300785 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.[CH3:35][O:36][C:37]1[CH:43]=[CH:42][C:40]([NH2:41])=[CH:39][CH:38]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:35][O:36][C:37]1[CH:43]=[CH:42][C:40]([NH:41][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])=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 7732P-AnisidineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69962054HCID 69962054, compound

Product 1

HCID 59924908HCID 59924908, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-[(S)-1-(3-carboxyphenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine (28.9 mg) was dissolved in CH2Cl2 (2 mL), then triethylamine (55 μL) was added followed by 4-methoxyaniline (62 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (53.4 mg) and 4-dimethylaminopyridine (˜1 mg). The mixture was stirred at room temperature for 18 h then directly eluted on silica gel column (1-4% MeOH:CH2Cl2) to yield 19.7 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.45 (br s, 1H); 8.37 (d, J=5.5 Hz, 1H); 7.99 (s, 1H); 7.88 (s, 1H); 7.80 (d, J=6.2 Hz, 1H); 7.75 (d, J=7.5 Hz, 1H); 7.62 (d, J=7.8 Hz, 1H); 7.49 (m, 3H); 7.33 (m, 2H); 6.90 (d, J=8.9 Hz, 2H); 6.77 (d, J=5.5 Hz, 1H); 5.87 (br s, 1H); 5.26 (br s, 1H); 3.81 (s, 3H); 1.65 (d, J=6.8 Hz, 3H). Mass Spectrum (ESI): m/e 465.2 (M+1).

Workup

  1. washthen directly eluted on silica gel column (1-4% MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-95a83afd30564abfafcb874c53a009f7
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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