5-Aminobenzimidazole → HCID 178486802, compound

HRID 1595797Notes

Reaction equation

HRID 1595797 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[NH2:18][C:19]1[CH:27]=[CH:26][C:22]2[N:23]=[CH:24][NH:25][C:21]=2[CH:20]=1.Cl.N1C=CC=CC=1>C(OCCO)C>[NH:23]1[C:22]2[CH:26]=[CH:27][C:19]([NH:18][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][C:3]=3[C:16]#[N:17])=[CH:20][C:21]=2[N:25]=[CH:24]1

Participants

5

Reactant 3

HCID 136235-AminobenzimidazoleHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 178486802HCID 178486802, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

Using an analogous procedure to that described in Example 150, 248.7 mg (1 mmol) of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile, 159.8 mg (1.2 mmol) of 5-aminobenzimdazole and 115.6 mg (1 mmol) of pyridine hydrochloride in 10 mL of 2-ethoxyethanol was refluxed for 1 hr. The work up gave 233.6 mg (67.7%) of the product as a brown solid, m.p. 230°0 C. (dce.), mass (electrospray, m/e): M+H 345.9. HRCIMS: calcd 346.1304 for C19H15N5O2 (M+), obsd 346.1325.

Workup

  1. temperaturewas refluxed for 1 hr

Sources & evidence

ORD record
ord-9a5e25523e074df08a5f107fee925892
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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