2-Aminothiazole → 2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)-N-thiazol-2-ylpropionamide

HRID 14989

반응식

HRID 14989 반응식
[CH3:1][N:2]1[C:15]2[CH:14]=[C:13]([CH:16]([CH2:20][CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:17](O)=[O:18])[CH:12]=[CH:11][C:10]=2[S:9](=[O:28])(=[O:27])[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[NH2:29][C:30]1[S:31][CH:32]=[CH:33][N:34]=1.C(N(CC)C(C)C)(C)C.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][N:2]1[C:15]2[CH:14]=[C:13]([CH:16]([CH2:20][CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:17]([NH:29][C:30]3[S:31][CH:32]=[CH:33][N:34]=3)=[O:18])[CH:12]=[CH:11][C:10]=2[S:9](=[O:28])(=[O:27])[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

참가 물질

7

반응물 4

HCID 21552-AminothiazoleHCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 580242342-(10-Methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)propionic acid

생성물 1

HCID 250091012-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)-N-thiazol-2-ylpropionamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

200 mg of 2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)propionic acid, 74.8 mg of commercially available 2-aminothiazole and 220 μl of N,N-diisopropylethylamine are dissolved in 10 ml of dimethylformamide. 212 mg of TOTU are added, and the mixture is stirred at room temperature overnight. The reaction mixture is then diluted by addition of 50 ml of ethyl acetate and washed five times with in each case 30 ml of saturated sodium bicarbonate solution. The organic phase is dried over MgSO4, and the solvent is then removed under reduced pressure. The residue is purified by RP-HPLC. This gives 141 mg of 2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)-N-thiazol-2-ylpropionamide as a colorless lyophilisate.

후처리

  1. washwashed five times with in each case 30 ml of saturated sodium bicarbonate solution
  2. dry with materialThe organic phase is dried over MgSO4
  3. customthe solvent is then removed under reduced pressure
  4. customThe residue is purified by RP-HPLC

출처 및 근거

ORD 기록
ord-b0f28dd913ac49b39384885491f565e4
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732440B2

연결된 노트

불러오는 중…