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1-Hydroxybenzotriazole → 2-(N-Methylcarbamoyl)-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]-4-[(6-trimethylsilylethynylbenzo[b]thien-2-yl)sulfonyl]piperazine

HRID 352968
ノート
印刷プレビュー

反応式

HRID 352968 の反応式
[CH3:1][NH:2][C:3]([CH:5]1[NH:10][CH2:9][CH2:8][N:7]([S:11]([C:14]2[S:18][C:17]3[CH:19]=[C:20]([C:23]#[C:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:21]=[CH:22][C:16]=3[CH:15]=2)(=[O:13])=[O:12])[CH2:6]1)=[O:4].[CH3:29][CH:30]1[NH:35][CH2:34][C:33]2[S:36][C:37]([C:39]([O-])=[O:40])=[N:38][C:32]=2[CH2:31]1.[Li+].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(Cl)Cl>[CH3:1][NH:2][C:3]([CH:5]1[CH2:6][N:7]([S:11]([C:14]2[S:18][C:17]3[CH:19]=[C:20]([C:23]#[C:24][Si:25]([CH3:26])([CH3:28])[CH3:27])[CH:21]=[CH:22][C:16]=3[CH:15]=2)(=[O:13])=[O:12])[CH2:8][CH2:9][N:10]1[C:39]([C:37]1[S:36][C:33]2[CH2:34][NH:35][CH:30]([CH3:29])[CH2:31][C:32]=2[N:38]=1)=[O:40])=[O:4]
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 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 227106073-(N-methylcarbamoyl)-1-[(6-trimethylsilylethynylbenzo[b]thien-2-yl)sulfonyl]piperazineHCID 23674323Lithium 6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate

生成物 1

HCID 22710415
2-(N-Methylcarbamoyl)-1-[(6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]-4-[(6-trimethylsilylethynylbenzo[b]thien-2-yl)sulfonyl]piperazine

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

In N,N-dimethylformamide (5 ml) was dissolved 3-(N-methylcarbamoyl)-1-[(6-trimethylsilylethynylbenzo[b]thien-2-yl)sulfonyl]piperazine (218 mg), followed by the addition of lithium 6-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate (188 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (240 mg) and 1-hyroxybenzotriazole (68 mg). The resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with methylene chloride, washed with water (twice) and then with a saturated aqueous solution of sodium bicarbonate. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (methanol:methylene chloride=3:97→5:95→7:93), whereby the title compound (90 mg) was obtained. MS (FAB) m/z: 616 (M+H)+.

後処理

  1. washwashed with water (twice) and then with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialAfter drying over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by chromatography on a silica gel column (methanol:methylene chloride=3:97→5:95→7:93), whereby the title compound (90 mg)
  5. customwas obtained

出典と根拠

ORDレコード
ord-f3da2f299e164268b07e0b240d8d9afa
出典データセット
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06747023B1

反応ノート

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