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Phenyl 2-(7-amino-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl(methyl)carbamate → Phenyl methyl(2-(7-(thiophene-2-carboximidamido)-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)carbamate

HRID 424488
ノート
印刷プレビュー

反応式

HRID 424488 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH2:11][CH2:12][N:13]([CH3:23])[C:14](=[O:22])[O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:9][CH2:8][S:7][C:6]=2[CH:24]=1.I.[S:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[C:31](SC)=[NH:32]>C(O)C.O.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:23][N:13]([CH2:12][CH2:11][N:10]1[CH2:9][CH2:8][S:7][C:6]2[CH:24]=[C:2]([NH:1][C:31]([C:27]3[S:26][CH:30]=[CH:29][CH:28]=3)=[NH:32])[CH:3]=[CH:4][C:5]1=2)[C:14](=[O:22])[O:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 59144153Phenyl 2-(7-amino-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl(methyl)carbamateHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

生成物 1

HCID 178484232Phenyl methyl(2-(7-(thiophene-2-carboximidamido)-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)carbamate収率 68.3%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water
溶媒
HCID 10340Sodium Carbonate溶媒

実験手順

To a stirred solution of phenyl 2-(7-amino-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl(methyl)carbamate (80 mg, 0.233 mmol) in ethanol (5 mL) under argon was added methyl thiophene-2-carbimidothioate hydroiodide (133 mg, 0.466 mmol). The mixture was then stirred overnight at room temperature. The mixture was then diluted with water and sodium carbonate and then extracted with dichloromethane (2×). The combined organics were dried, filtered, concentrated, and then chromatographed in ethyl acetate, yielding the desired product (72 mg, 68%). 1H NMR (DMSO-d6) δ 7.74-7.69 (m, 1H), 7.58-7.56 (m, 1H), 7.42-7.34 (m, 2H), 7.25-7.17 (m, 1H), 7.14-7.05 (m, 3H), 6.83-6.80 (m, 1H), 6.53-6.44 (m, 2H), 6.36 (brs, 2H), 3.63-3.55 (m, 4H), 3.49-3.45 (m, 2H), 3.11, 2.98 (2s, 3H), 3.06-3.01 (m, 2H); MS-EI: (m/z, %) 452 (M+, 97), 288 (100).

後処理

  1. extractionextracted with dichloromethane (2×)
  2. customThe combined organics were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed in ethyl acetate

出典と根拠

ORDレコード
ord-74315e1ca67c44f98a5452d34a8b1c28
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08106043B2

反応ノート

読み込み中…

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