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

HRID 14989
ノート
印刷プレビュー

反応式

HRID 14989 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b0f28dd913ac49b39384885491f565e4
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07732440B2

反応ノート

読み込み中…

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