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3-Methoxypropylamine → N-(3-methoxypropyl)-2-(2-phenylpyrimidin-5-yl)thiazole-4-carboxamide

HRID 42315
ノート
印刷プレビュー

反応式

HRID 42315 の反応式
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[S:14][CH:15]=[C:16]([C:18]([OH:20])=O)[N:17]=3)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:42][O:43][CH2:44][CH2:45][CH2:46][NH2:47].C(N(C(C)C)CC)(C)C>ClCCl>[CH3:42][O:43][CH2:44][CH2:45][CH2:46][NH:47][C:18]([C:16]1[N:17]=[C:13]([C:10]2[CH:11]=[N:12][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8][CH:9]=2)[S:14][CH:15]=1)=[O:20]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 16723-MethoxypropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 592524752-(2-Phenylpyrimidin-5-yl)thiazole-4-carboxylic acid

生成物 1

HCID 59252401N-(3-methoxypropyl)-2-(2-phenylpyrimidin-5-yl)thiazole-4-carboxamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution consisting of 2-(2-phenylpyrimidin-5-yl)thiazole-4-carboxylic acid (Example 63, 80 mg, 0.28 mmol) in dichloromethane (10 mL) was added EDAC (75 mg, 0.39 mmol) and HOBt (53 mg, 0.39 mmol) at 0° C. To this mixture was added 3-methoxypropylamine (25 mg, 0.28 mmol) dissolved in dichloromethane (2 mL) and diisopropylethylamine (0.52 mL, 390 mg, 3.0 mmol). The solution was allowed to reach room temperature and stirred for 18 hours. The solvent was evaporated away under reduced pressure and the residue was purified by silica gel flash chromatography (1:1 v/v hexane-ethyl acetate to 100% ethyl acetate gradient) through a 25-g Silicycle® flash silica cartridge. The title compound was obtained as an off-white solid (21 mg, 21% yield); Rf 0.70 with 4:1 v/v ethyl acetate-hexane; melting point 134-136° C.; 1H-NMR (300 MHz; CDCl3) δ 9.31 (s, 2H), 8.52 (dd, 2H), 8.20 (s, 1H), 7.88 (br t, 1H), 7.53 (m, 3H), 3.62 (t, 2H); 3.59 (t, 2H); 3.41 (s, 3H), 1.96 (m, 2H); MS (ESI+) m/z 355 (M+1); H-PGDS FPBA IC50: 3.4 μM.

後処理

  1. customto reach room temperature
  2. customThe solvent was evaporated away under reduced pressure
  3. customthe residue was purified by silica gel flash chromatography (1:1 v/v hexane-ethyl acetate to 100% ethyl acetate gradient) through a 25-g Silicycle® flash silica cartridge

出典と根拠

ORDレコード
ord-ad6c6539b9aa414784569152efc8236a
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08536185B2

反応ノート

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