2-Chloro-5-methoxy-1H-benzimidazole → HCID 178488095, compound

HRID 1274153Notes

Reaction equation

Cl[C:2]1[NH:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:13]([O:17][C:18](=[O:32])[C:19]1[CH:24]=[CH:23][C:22]([NH:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:21][CH:20]=1)([CH3:16])([CH3:15])[CH3:14]>C(O)CCCC>[C:13]([O:17][C:18](=[O:32])[C:19]1[CH:24]=[CH:23][C:22]([NH:25][CH:26]2[CH2:31][CH2:30][N:29]([C:2]3[NH:6][C:5]4[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:4]=4[N:3]=3)[CH2:28][CH2:27]2)=[CH:21][CH:20]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

Conditions

Temperature: 120 °C

Procedure

2-Chloro-5-methoxybenzimidazole (0.089 g, 0.49 mmol) was added to a solution of (49) (0.14 g, 0.5 mmol) in n-pentanol (3 mL) at 25° C. The mixture was heated to 120° C. and was maintained at that temperature for 12 h. The reaction mixture was cooled to room temperature and the desired product was filtered and rinsed with acetone to give 0.17 g (83.3%) of the title compound: TLC (Rf =0.30; 5% MeOH/CH2Cl2); 1H NMR (DMSO) δ 13.40 (br s, 1H), 7.63 (d, 2H, J=8.3), 7.29 (d, 1H, J=8.7), 6.91 (s, 1H), 6.83 (d, 1H, J=8.4), 6.65 (d, 2H, J=8.3), 6.50 (s, 1H), 4.13 (d, 2H, J=12.7), 3.77 (s, 3H), 3.73 (m, 1H), 3.47 (m, 4H), 2.06 (d, 2H, J=11.0), 1.48 (s, 9H); 13C NMR (DMSO) δ 165.2, 156.1, 151.3, 149.8, 131.0, 130.9, 124.0, 117.8, 111.8, 111.3, 110.2, 96.4, 79.0, 55.7, 47.3, 45.6, 30.2, 30.0; HRMS (FAB) m/z 423.2388 (M+H)+ (C24H30N4O3 requires 423.2389); Anal. (C24H30N4O3 ·1HCl·1/2H2O) C, H, N.

Workup

temperaturewas maintained at that temperature for 12 h
temperatureThe reaction mixture was cooled to room temperature
filtrationthe desired product was filtered
washrinsed with acetone

Sources & evidence

ORD record: ord-5781c3ab317b4723874364f6ee1cc21b
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156758

Reaction notes

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