Sodium Bicarbonate → HCID 178511960, 화합물

HRID 1186292노트

반응식

HRID 1186292 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][OH:19])[CH2:13][CH:12]=1.I.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26](SC)=[NH:27].C([O-])(O)=O.[Na+]>C(O)C>[OH:19][CH2:18][CH2:17][N:14]1[CH2:15][CH:16]=[C:11]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:26]([C:22]4[S:21][CH:25]=[CH:24][CH:23]=4)=[NH:27])[CH:3]=3)[NH:7][CH:6]=2)[CH2:12][CH2:13]1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 577918722-(4-(5-amino-1H-indol-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanolHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

생성물 1

HCID 178511960HCID 178511960, 화합물수율 61.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 2-(4-(5-amino-1H-indol-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanol (0.16 g, 0.622 mmol) in dry ethanol (5 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.355 g, 1.244 mmol) at room temperature and stirred overnight (18 h). The reaction was basified with sat. NaHCO3 solution (50 mL) and product was extracted into CH2Cl2 (3×20 mL). The combined CH2Cl2 layer was washed with brine (20 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:9) to obtain N-(3-(1-(2-hydroxyethyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)thiophene-2-carboximidamide (0.14 g, 61.4%) as a solid. 1H NMR (DMSO-d6) δ 10.92 (s, 1H), 7.71 (d, 1H, J=3.6 Hz), 7.58 (d, 1H, J=5.1 Hz), 7.33-7.30 (m, 2H), 7.21 (s, 1H), 7.09 (t, 1H, J=3.9 Hz), 6.66 (d, 1H, J=8.4 Hz), 6.23 (brs, 2H), 6.03 (s, 1H), 4.40 (t, 1H, J=5.1 Hz), 3.54 (q, 2H), 3.16-3.10 (m, 2H), 2.66 (t, 2H, J=5.4 Hz), 2.50-2.44 (m, 4H, merged with DMSO-peak); ESI-MS (m/z, %): 367 (MH+, 33), 294 (100).

후처리

  1. extractionwas extracted into CH2Cl2 (3×20 mL)
  2. washThe combined CH2Cl2 layer was washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. customSolvent was evaporated
  5. customcrude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:9)

출처 및 근거

ORD 기록
ord-f3a01419f2fa4952ace7554606a14754
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673909B2

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