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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 1917145
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HRID 1917145 반응식
[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
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참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water
용매
HCID 10340Sodium Carbonate용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-0a98bb7702184c07849458133246a48b
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08618286B2

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