2-Dimethylaminopyridine → HCID 22119992, 화합물

HRID 1274648노트

반응식

HRID 1274648 반응식
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21]([CH3:26])([CH3:25])[C:22](O)=[O:23])[C:17]=3[CH:27]=2)[C:3]1=[O:28].C(Cl)(=O)C(Cl)=O.[CH3:35][S:36]([NH2:39])(=[O:38])=[O:37].C(N(C(C)C)C(C)C)C.CN(C1C=CC=CN=1)C>CN(C)C=O.C(Cl)Cl>[CH3:1][N:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([C:21]([CH3:26])([CH3:25])[C:22]([NH:39][S:36]([CH3:35])(=[O:38])=[O:37])=[O:23])[C:17]=3[CH:27]=2)[C:3]1=[O:28]

참가 물질

8

반응물 5

HCID 218852-DimethylaminopyridineHCID 65578Oxalyl chlorideHCID 72879MethanesulfonamideHCID 81531DiisopropylethylamineHCID 22119820HCID 22119820, 화합물

생성물 1

HCID 22119992HCID 22119992, 화합물수율 13.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

N,N-Dimethylformamide (8 drops) is added to a mixture of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-α,α-dimethyl-1,2-benzisothiazole-3-acetic acid (2.00 g, 0.00484 mol) and methylene chloride. The mixture is cooled on an ice bath and oxalyl chloride (2.0 M in methylene chloride, 6.05 ml, 0.0121 mol) is added. The resultant mixture is stirred one hour on an ice bath and concentrated in vacuo. The residue is taken up in tetrahydrofuran. Methylsulfonamide (0.690 g, 0.00726 mol) is added, followed by ethyldiisopropylamine (0.940 g, 0.00727 mol) and dimethylaminopyridine (0.100 g). The resultant mixture is stirred at room temperature and filtered. The filtrate is concentrated in vacuo and the residue is filtered through silica gel with hexanes:ethyl acetate. The filtrate is concentrated in vacuo to a tan solid. The solid is suspended in methylene chloride, stirred, and refiltered to give the title compound as a white solid (0.320 g, 13.5%, mp 264-265° C.).

후처리

  1. temperatureThe mixture is cooled on an ice bath
  2. concentrationconcentrated in vacuo
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated in vacuo
  5. filtrationthe residue is filtered through silica gel with hexanes
  6. concentrationThe filtrate is concentrated in vacuo to a tan solid

출처 및 근거

ORD 기록
ord-8fab8baf12804d5089e953babd489946
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06156700

반응 노트

불러오는 중…