Glycol monoethyl ether → HCID 178486709, compound

HRID 1595801Notes

Reaction equation

HRID 1595801 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[NH:23][N:24]=[N:25][C:21]=2[CH:20]=1.Cl.N1C=CC=CC=1.[CH2:35]([O:37]CCO)C>>[N:23]1[C:22]2[CH:26]=[CH:27][C:19]([NH:18][C:2]3[C:11]4[C:6](=[C:7]([O:37][CH3:35])[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[NH:25][N:24]=1

Participants

5

Reactant 4

HCID 8076Glycol monoethyl etherHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrileHCID 178507366HCID 178507366, compound

Product 1

HCID 178486709HCID 178486709, compound

Procedure

Using an analogous procedure to that described in Example 150, 278.7 mg (1 mmol) of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile, 161.3 mg (1.2 mmol) of 5-aminobenzotriazole and 115.6 mg (1 mmol) of pyridine hydrochloride in 10 mL of 2-ethoxyethanol was refluxed for 10 min. The work up gave 246.3 mg (65.4%) of the product as a yellow solid, m.p. 205° C. (dec.), mass (electrospray, m/e): M+H 376.9. HRCIMS: calcd 376.128 for C19H16N6O3(M+), obsd 376.1264.

Workup

  1. temperaturewas refluxed for 10 min

Sources & evidence

ORD record
ord-01157ed0a4a14351acba201a76943cd8
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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