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3-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)-1H-indol-5-amine → HCID 178511959、化合物

HRID 2223814
ノート
印刷プレビュー

反応式

HRID 2223814 の反応式
CN[CH:3]1[CH2:8][CH2:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([NH:18][C:19]([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)=[NH:20])[CH:16]=3)[NH:11][CH:10]=2)=[CH:5][CH2:4]1.C1C2[N:29]([CH2:30]C=C(C3C4C(=CC=C(N)C=4)NC=3)C2)[CH2:28]C1.I.CSC(C1SC=CC=1)=N>C(O)C>[CH2:3]1[CH:4]2[N:29]([CH2:30][CH:7]=[C:6]([C:9]3[C:17]4[C:12](=[CH:13][CH:14]=[C:15]([NH:18][C:19]([C:21]5[S:22][CH:23]=[CH:24][CH:25]=5)=[NH:20])[CH:16]=4)[NH:11][CH:10]=3)[CH2:5]2)[CH2:28][CH2:8]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 537825203-(1,2,3,5,8,8a-hexahydroindolizin-7-yl)-1H-indol-5-amineHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodideHCID 178482098HCID 178482098、化合物

生成物 1

HCID 178511959HCID 178511959、化合物収率 79%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of compound 141 (0.12 g, 0.423 mmol) in dry methanol (5 mL) was treated with Ra—Ni (˜0.05 g), hydrazine hydrate (0.13 mL, 4.235 mmol) at room temperature. The resulting mixture was refluxed for 2 min, in pre-heated oil bath. The reaction was brought to room temperature, filtered through celite bed and washed with methanol (2 20 m L). The combined methanol layer was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH: CH2Cl2, 95:5) to obtain 3-(1,2,3,5,8,8a-Hexahydroindolizin-7-yl)-1H-indol-5-amine, (0.087 g, 81%) as a solid. mp 208-210° C.; 1H NMR (DMSO-d6) δ 1.33-1.48 (m, 1H), 1.67-1.79 (m, 2H), 1.94-2.13 (m, 2H), 2.16-2.26 (m, 2H), 2.58-2.65 (m, 1H), 2.85 (d, 1H, J=15.6 Hz), 3.08-3.17 (m, 1H), 3.59 (dd, 1H, J=4.5, 15.7 Hz), 4.49 (s, 2H), 6.01 (d, 1H, J=4.5 Hz), 6.48 (dd, 1H, J=1.8, 9.1 Hz), 7.01 (d, 1H, J=1.5 Hz), 7.05 (d, 1H, J=8.4 Hz), 7.17 (d, 1H, J=2.7 Hz), 10.60 (s, 1H); ESI-MS (m/z, %) 254 (MH+, 62), 185 (100). A solution of the amine (0.053 g, 0.209 mmol) in dry ethanol (3 mL) was treated with thiophene-2-carboximidothioic acid methyl ester hydroiodide (0.12 g, 0.418 mmol) at room temperature and the solution was stirred for 24 h. Solvent was evaporated, crude was diluted with sat. NaHCO3 solution (20 mL) and product was extracted into CH2Cl2 (2 20 mL). The combined CH2Cl2 layer was washed with brine (15 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH: CH2Cl2, 5:95) to obtain compound 142 (0.06 g, 79%) as a solid. mp 122-124° C.; 1H NMR (DMSO-d6) δ 1.38-1.46 (m, 1H), 1.70-1.78 (m, 2H), 1.93-2.12 (m, 2H), 2.20-2.28 (m, 2H), 2.62-2.72 (m, 1H), 2.83 (d, 1H, J=15.9 Hz), 3.07-3.13 (m, 1H), 3.59 (dd, 1H, J=4.5, 16.0 Hz), 6.07 (d, 1H, J=3.9 Hz), 6.22 (brs, 2H), 6.66 (d, 1H, J=8.1 Hz), 7.09 (dd, 1H, J=3.9, 4.9 Hz), 7.22 (s, 1H), 7.30-7.32 (m, 2H), 7.58 (d, 1H, J=4.5 Hz), 7.71 (d, 1H, J=2.7 Hz), 10.92 (s, 1H); ESI-MS (m/z, %) 363 (MH+, 20), 294 (100), 182 (15); ESI-HRMS calculated for C21H23N4S (MH+), calculated: 363.1655; observed: 363.1637.

後処理

  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 was washed with brine (15 mL)
  5. dry with materialdried (Na2SO4)
  6. customSolvent was evaporated
  7. customcrude was purified by column chromatography (2 M NH3 in MeOH: CH2Cl2, 5:95)

出典と根拠

ORDレコード
ord-479c5fbfbbbb4648a9b135eb23b180df
出典データセット
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07375219B2

反応ノート

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