Methylamine → HCID 178485736, 화합물

Trans-4-(4-nitro-3-trifluoromethyl-phenylamino)-cyclohexanecarboxylic acid (500 mg, 1.50 mmol, prepared in accordance with Example 42), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (570 mg, 1.5 mmol), and diisopropylethylamine (600 μL, 3.30 mmol) were dissolved in dry tetrahydrofuran (10 mL). The resulting mixture was stirred at room temperature for 10 min, and then cooled to 0° C. A solution of methylamine in tetrahydrofuran (750 μL, 2M, 1.50 mmol) and dimethylformamide (1 mL) was added, and the resulting mixture was stirred at room temperature for 3 hr. The mixture was then concentrated under vacuum. The resulting residue was taken up in dichloromethane (25 mL), and the organic phase was washed with water (10 mL), and then with aqueous saturated hydrogencarbonate (3×10 mL). The organic layer was collected, dried over magnesium sulfate, filtered, and concentrated under vacuum. The residue was diluted in dioxane (5 mL), and a concentrated solution of HCl in dioxane was added (10 mL, 4N). A precipitate formed, which was then washed with diethylether (10 mL) and dried under vacuum. The desired product was isolated as a yellow solid (498 mg, 87% yield).

1. temperaturecooled to 0° C
2. stirringthe resulting mixture was stirred at room temperature for 3 hr
3. concentrationThe mixture was then concentrated under vacuum
4. washthe organic phase was washed with water (10 mL)
5. customThe organic layer was collected
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under vacuum
9. additionThe residue was diluted in dioxane (5 mL)
10. additiona concentrated solution of HCl in dioxane was added (10 mL, 4N)
11. customA precipitate formed
12. washwhich was then washed with diethylether (10 mL)
13. customdried under vacuum

ORD 기록

ord-8a54b4faccb14e3bae45a7ea9038b3da

출처 데이터셋

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08569495B2