Triethylamine → 4-({Ethyl-[7-(4-methanesulfonyl-benzoylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-amino}-methyl)-piperidine-1-carboxylic acid isopropylamide

To an ice-cold solution of N-[7-(ethyl-piperidin-4-ylmethyl-amino)-5,6,7,8-tetrahydro-naphthalen-2-yl]-4-methanesulfonyl-benzamide (1.3 g, 2.3 mmol) in methylene chloride (40 mL) under a nitrogen atmosphere was added the triethylamine (1.3 mL, 9.2 mmol, 4 eq.) in a single portion followed by the isopropylisocyanate (0.33 mL, 3.3 mmol, 1.4 eq). The reaction was allowed to warm to room temperature and stirred for 24 h. The reaction was concentrated in vacuo and partitioned between EtOAc (75 mL) and 10% aq. sodium hydroxide (40 mL). The aqueous layer was extracted with EtOAc (2×30 mL) and the combined EtOAc layers were dried over MgSO4, filtered, and concentrated. Trituration with ether afforded 4-({ethyl-[7-(4-methanesulfonyl-benzoylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-amino}-methyl)-piperidine-1-carboxylic acid isopropylamide 1 as a light pink solid (1.1 g). [M+H]+=555.

1. concentrationThe reaction was concentrated in vacuo
2. custompartitioned between EtOAc (75 mL) and 10% aq. sodium hydroxide (40 mL)
3. extractionThe aqueous layer was extracted with EtOAc (2×30 mL)
4. dry with materialthe combined EtOAc layers were dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated

ORD 기록

ord-f4b0e2d23c6e47f5b6229ff207f2b141

출처 데이터셋

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06864266B2