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

반응식

HRID 2230806 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-580f3370a3e74d03a61357e74fca06ee
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06426357B1

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