Tryptamine → 3-[(2S*,5R*)-5-{[2-(1H-Indol-3-yl)-ethylcarbamoyl]-methyl}-4-oxo-2-(5-phenylethynyl-thiophen-2-yl)-thiazolidin-3-yl]-propionamide

HRID 2230806

反応式

HRID 2230806 の反応式
[C:1]([CH2:4][CH2:5][N:6]1[C:10](=[O:11])[CH:9]([CH2:12][C:13](O)=[O:14])[S:8][CH:7]1[C:16]1[S:17][C:18]([C:21]#[C:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][CH:20]=1)(=[O:3])[NH2:2].[NH:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([CH2:38][CH2:39][NH2:40])=[CH:30]1.C(P(=O)(OCC)OCC)#N.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[NH:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([CH2:38][CH2:39][NH:40][C:13]([CH2:12][C@H:9]2[S:8][C@@H:7]([C:16]3[S:17][C:18]([C:21]#[C:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:19][CH:20]=3)[N:6]([CH2:5][CH2:4][C:1]([NH2:2])=[O:3])[C:10]2=[O:11])=[O:14])=[CH:30]1

参加物

7

反応物 4

HCID 1150TryptamineHCID 76257Diethyl cyanophosphonateHCID 81531DiisopropylethylamineHCID 86758382[3-(2-Carbamoyl-ethyl)-4-oxo-2-(5-phenylethynyl-thiophen-2-yl)-thiazolidin-5-yl]-acetic acid

生成物 1

HCID 867583833-[(2S*,5R*)-5-{[2-(1H-Indol-3-yl)-ethylcarbamoyl]-methyl}-4-oxo-2-(5-phenylethynyl-thiophen-2-yl)-thiazolidin-3-yl]-propionamide収率 16.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of [3-(2-carbamoyl-ethyl)-4-oxo-2-(5-phenylethynyl-thiophen-2-yl)-thiazolidin-5-yl]-acetic acid (1.36 g,3.28 mmol), 3-indolylethylamine (0.77 g, 4.8 mmol), diethyl cyanophosphonate (0.781 g, 4.8 mmol) and diisopropylethylamine (0.62 g, 4.8 mmol) was stirred in DMF (50 mL) for three hours at room temperature. The mixture was poured into water (100 mL). The product was extracted into ethyl acetate (2×100 mL). The extract was washed successively with sat. NaHCO3, H2O, brine, and then dried (MgSO4). The solvent was evaporated to a brown gum, which was washed twice with methanol to remove the dark color to provide the title compound as an off-white solid (0.3 g, 16.8%). 1H NMR (DMSO-d6) δ 10.8 (s, 1H), 8.19-8.23 (t, 1H), 7.51-7.55 (m, 3H), 7.33-7.46 (m, 4H), 7.27-7.31 (m, 3H), 7.14-7.15 (d, 1H, J=2.2 Hz), 7.02-7.07 (t, 1H), 6.91-6.98 (m, 2H), 6.13 (s, 1H ), 4.15-4.20 (dd, 1H, J=3.1 Hz ), 3.55-3.64 (m, 1H), 3.27-3.41 (m, 2H), 2.97-3.07 (m, 2H), 2.79-2.84 (t, 2H), 2.60 (s, 1H), 2.55-2.56 (d, 1H, J=4.7 Hz), 2.35-2.45 (m,1H), 2.08-2.18 (m, 1H), 95% cis based on peaks at δ 6.13 and 4.15-4.20); MS(ESI)557[M+H]+.FTIR(ATR) 1620, 1660 cm−1.Anal.(C30H28N4O3S2) calc. C, 64.72; H, 5.07; N, 10.06. Obs. C, 64.55; H, 4.98; N, 9.93.

後処理

  1. extractionThe product was extracted into ethyl acetate (2×100 mL)
  2. washThe extract was washed successively with sat. NaHCO3, H2O, brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated to a brown gum, which
  5. washwas washed twice with methanol
  6. customto remove the dark color

出典と根拠

ORDレコード
ord-580f3370a3e74d03a61357e74fca06ee
出典データセット
uspto-grants-2002_07
特許番号
US06426357B1

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