Dimethyl Sulfoxide → (r)-6-Methyl-4'-trifluoromethylbiphenyl-2-carboxylic acid (2-methoxycarbonylaminoindan-5-yl)-amide

HRID 1814783노트

반응식

HRID 1814783 반응식
[CH3:1][O:2][C:3](=[O:15])[NH:4][C@H:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:14])[CH:11]=2)[CH2:6]1.CS(C)=O.N1C=CC=CC=1.[CH3:26][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]([C:43](Cl)=[O:44])[C:32]=1[C:33]1[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=1>C(Cl)Cl>[CH3:1][O:2][C:3]([NH:4][C@H:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:14][C:43]([C:31]3[C:32]([C:33]4[CH:38]=[CH:37][C:36]([C:39]([F:40])([F:42])[F:41])=[CH:35][CH:34]=4)=[C:27]([CH3:26])[CH:28]=[CH:29][CH:30]=3)=[O:44])[CH:11]=2)[CH2:6]1)=[O:15]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 110556396-Methyl-4'-trifluoromethylbiphenyl-2-carboxylic acid chlorideHCID 11413084(R)-Methyl (5-amino-2,3-dihydro-1H-inden-2-yl)carbamate

생성물 1

HCID 9869236(r)-6-Methyl-4'-trifluoromethylbiphenyl-2-carboxylic acid (2-methoxycarbonylaminoindan-5-yl)-amide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To an ice bath cooled solution of (R)-(5-aminoindan-2-yl)-carbamic acid methyl ester (9.5 g, 46.1 mmol), ([α]D=−26.29° (c=9.87 mg/mL, DMSO); mp 144-145° C.) and pyridine (4.48 mL, 55.5 mmol) in 200 mL of methylene chloride is added 6-methyl-4′-trifluoromethyl-1,1′-biphenyl-2-carboxylic acid chloride (80.5 mL of a 0.63 M solution in methylene chloride, 50.7 mmol). The reaction is stirred for 15 minutes at room temperature. The mixture is washed with 1N HCl, bicarbonate and brine. The organic layer is dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The product is purified by crystallization from ethyl acetate/hexanes (1:2) to give (R)-6-methyl-4′-trifluoromethyl-1,1′-biphenyl-2-carboxylic acid (2-methoxycarbonylaminoindan-5-yl)-amide as crystalline solid, mp 112-114° C. [α]D=−12.85°, c=11.36 mg/mL DMSO.

후처리

  1. washThe mixture is washed with 1N HCl, bicarbonate and brine
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe product is purified by crystallization from ethyl acetate/hexanes (1:2)

출처 및 근거

ORD 기록
ord-ed002a230a3a49398b2d1075268f681e
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06878707B2

반응 노트

불러오는 중…