2-Methylquinolin-6-amine → 1-(5-Cyclobutyl-thiazol-2-yl)-3-(2-methyl-quinolin-6-yl)-urea

HRID 2085492Notes

Reaction equation

HRID 2085492 reaction equation
C1(O[C:8](=[O:19])[NH:9][C:10]2[S:11][C:12]([CH:15]3[CH2:18][CH2:17][CH2:16]3)=[CH:13][N:14]=2)C=CC=CC=1.[NH2:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[N:27]=[C:26]([CH3:31])[CH:25]=[CH:24]2>O1CCOCC1>[CH:15]1([C:12]2[S:11][C:10]([NH:9][C:8]([NH:20][C:21]3[CH:22]=[C:23]4[C:28](=[CH:29][CH:30]=3)[N:27]=[C:26]([CH3:31])[CH:25]=[CH:24]4)=[O:19])=[N:14][CH:13]=2)[CH2:16][CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 1031482-Methylquinolin-6-amineHCID 9965366(5-Cyclobutyl-thiazol-2-yl)-carbamic acid phenyl ester

Product 1

HCID 99676931-(5-Cyclobutyl-thiazol-2-yl)-3-(2-methyl-quinolin-6-yl)-ureaYield 92.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (5-cyclobutyl-thiazol-2-yl)-carbamic acid phenyl ester (Example 2; 35 mg, 0.128 mmol) and 6-amino-2-methyl-quinoline (50 mg, 0.128 mmol) in 1,4-dioxane (500 μl) were heated at about 70° C. for 24 hours. Purification by silica gel chromatography (1:3 hexanes-ethylacetate; 40:1→20:1 chloroform-methanol) and subsequent conversion to the HCl salt afforded 40 mg of the title compound. 1HNMR (400 MHz, CDCl3) δ 8.11(s,1H), 7.87 (s,7.88,1H), 7.85 (s,1H), 7.45 (d, J=7.6 Hz,1H), 7.16 (d, J=8.4 Hz, 1H), 6.94 (s,1H), 3.55 (m,1 H), 2.67 (s,3H), 2.35 (m,2H), 2.15-1.80 (m,4H). LRMS m/z (APCl+) 339.0 (M+H)+.

Workup

  1. customPurification by silica gel chromatography (1:3 hexanes-ethylacetate; 40:1→20:1 chloroform-methanol) and subsequent conversion to the HCl salt

Sources & evidence

ORD record
ord-40421a6fc5594a228e91243b5f7310cc
Source dataset
uspto-grants-2004_04
Patent number
US06720427B2

Reaction notes

Loading…