4-Chloroaniline → HCID 59924769, compound

HRID 2300784Notes

Reaction equation

HRID 2300784 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.[Cl:35][C:36]1[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:35][C:36]1[CH:42]=[CH:41][C:39]([NH:40][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:38][CH:37]=1

Participants

7

Reactant 4

HCID 78124-ChloroanilineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69962054HCID 69962054, compound

Product 1

HCID 59924769HCID 59924769, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-[(S)-1-(3-carboxyphenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine (38.1 mg) was dissolved in CH2Cl2 (2 mL), then triethylamine (73 μL) was added followed by 4-chloroaniline (58.9 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (58.0 mg) and 4-dimethylaminopyridine (˜1 mg). The mixture was stirred at room temperature for 45 min then eluted directly on silica gel column (98:2 CH2Cl2:MeOH) then on one 250 μm silica gel plate (1:1 hexanes:acetone) to yield 9.5 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.46 (br s, 1H); 8.39 (d, J=5.5 Hz, 1H); 7.98 (s, 1H); 7.90 (s, 1H); 7.82 (d, J=6.4 Hz, 1H); 7.75 (d, J=7.6 Hz, 1H); 7.65 (d, J=7.6 Hz, 1H); 7.58 (d, J=8.7 Hz, 2H); 7.51 (t, J=7.7 Hz, 1H); 7.33 (m, 3H); 6.80 (d, J=5.5 Hz, 1H); 5.94 (br s, 1H); 5.26 (br s, 1H); 1.67 (d, J=6.9 Hz, 3H). Mass Spectrum (ESI): m/e 469.2 (M+1).

Workup

  1. washthen eluted directly on silica gel column (98:2 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-b194914362d34eb5afc5b0024e4120aa
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

Loading…