Methyl thiophene-2-carbimidothioate hydroiodide → HCID 178465426, 화합물

HRID 1668500노트

반응식

HRID 1668500 반응식
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH2:16][CH2:15][CH:14]([N:17]([CH2:25][CH3:26])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13][CH:12]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.I.CS[C:30]([C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)=[NH:31]>CCO>[CH2:25]([N:17]([CH:14]1[CH2:15][CH2:16][C:11]([C:6]2[C:5]3[C:9](=[CH:10][C:2]([NH:1][C:30]([C:32]4[S:33][CH:34]=[CH:35][CH:36]=4)=[NH:31])=[CH:3][CH:4]=3)[NH:8][CH:7]=2)=[CH:12][CH2:13]1)[C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH3:26]

참가 물질

4

반응물 2

HCID 66704664Methyl thiophene-2-carbimidothioate hydroiodideHCID 68254813HCID 68254813, 화합물

생성물 1

HCID 178465426HCID 178465426, 화합물수율 75%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of above compound 130 in dry EtOH (5 mL) was treated with thiophene-2-carboximidothioic acid methyl ester hydroiodide (0.29 g, 1.037 mmol) at room temperature and stirred for 24 h. Solvent was evaporated and crude was diluted with sat. NaHCO3 solution (20 mL) and product was extracted into CH2Cl2 (2×20 mL). The combined CH2Cl2 layer washed with brine (15 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 5:95) to obtain compound 131 (0.18 g, 75%, over two steps) as a yellow solid. mp 110-112° C.; 1H NMR (DMSO-d6) δ 1.09 (t, 3H, J=6.6 Hz), 1.42 (s, 9H), 1.82-1.93 (m, 2H), 2.22-2.64 (m, 4H), 3.12-3.18 (m, 2H), 4.06 (brs, 1H), 6.10 (s, 1H), 6.32 (s, 2H), 6.60 (d, 1H, J=8.4 Hz), 6.82 (s, 1H), 7.09 (t, 1H, J=4.5 Hz), 7.23 (s, 1H), 7.59 (d, 1H, J=4.8 Hz), 7.68-7.73 (m, 2H), 10.84 (s, 1H); ESI-MS (m/z, %) 465 (MH+, 100).

후처리

  1. customSolvent was evaporated
  2. additioncrude was diluted with sat. NaHCO3 solution (20 mL) and product
  3. extractionwas extracted into CH2Cl2 (2×20 mL)
  4. washThe combined CH2Cl2 layer washed with brine (15 mL)
  5. dry with materialdried (Na2SO4)
  6. customSolvent was evaporated
  7. customcrude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 5:95)

출처 및 근거

ORD 기록
ord-dba117014ab04677938ff64bc93ca59c
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989447B2

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