Lithium Hydroxide → 4-(1-{[4-(4-Trifluoromethyl-benzyl)-4H-thieno[3,2-b]pyrrole-3-carbonyl]-amino}-cyclopropyl)-benzoic acid

A mixture of 0.33 g of 4-(4-Trifluoromethyl-benzyl)-4H-thieno[3,2-b]pyrrole-3-carboxylic acid, 0.23 g of 4-(1-amino-cyclopropyl)-benzoic acid methyl ester, 0.5 g of HATU and 0.25 ml of Pr2NEt in 8 ml of DMF was stirred at room temperature for 16 h. The reaction was then diluted with 30 ml of water and extracted with 100 ml of EtOAc. The organic layer was washed with 50 ml of water and 50 ml of brine and dried over Na2SO4. The extract was filtered, and concentrated to give the crude methyl ester which was dissolved in 20 ml of 1:1 THF/MeOH and treated with 10 ml of 0.5 N aqueous LiOH solution. After stirring for 15 h at room temperature, 1 ml of AcOH was added and the reaction mixture was extracted with 75 ml of EtOAc. The organic layer was washed with 50 ml of brine, dried over Na2SO4. The extract was filtered and concentrated to give 0.22 g of the title compound as a light brown solid.

1. extractionextracted with 100 ml of EtOAc
2. washThe organic layer was washed with 50 ml of water and 50 ml of brine
3. dry with materialdried over Na2SO4
4. filtrationThe extract was filtered
5. concentrationconcentrated
6. customto give the crude methyl ester which
7. stirringAfter stirring for 15 h at room temperature
8. extractionthe reaction mixture was extracted with 75 ml of EtOAc
9. washThe organic layer was washed with 50 ml of brine
10. dry with materialdried over Na2SO4
11. filtrationThe extract was filtered
12. concentrationconcentrated

ORD 기록

ord-f2f7cec5c5ea4ce1bad40dd591014656

출처 데이터셋

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08404736B2