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Triethylamine → {1-[6-Fluoro-4-(2-{5-fluoro-2-[2-(2-oxo-2,3-dihydro-imidazol-1-yl)-ethylamino]-pyrimidin-4-yl}-benzo[b]thiophen-7-yl)-pyridin-3-yl]-ethyl}-carbamic acid tert-butyl ester

HRID 561028
ノート
印刷プレビュー

反応式

HRID 561028 の反応式
[C:1]([O:5][C:6](=[O:34])[NH:7][CH:8]([C:10]1[CH:11]=[N:12][C:13]([F:33])=[CH:14][C:15]=1[C:16]1[C:21]2[S:22][C:23]([C:25]3[C:30]([F:31])=[CH:29][N:28]=[C:27](Cl)[N:26]=3)=[CH:24][C:20]=2[CH:19]=[CH:18][CH:17]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[NH2:35][CH2:36][CH2:37][N:38]1[CH:42]=[CH:41][NH:40][C:39]1=[O:43].C(N(CC)CC)C>CN1CCCC1=O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:34])[NH:7][CH:8]([C:10]1[CH:11]=[N:12][C:13]([F:33])=[CH:14][C:15]=1[C:16]1[C:21]2[S:22][C:23]([C:25]3[C:30]([F:31])=[CH:29][N:28]=[C:27]([NH:35][CH2:36][CH2:37][N:38]4[CH:42]=[CH:41][NH:40][C:39]4=[O:43])[N:26]=3)=[CH:24][C:20]=2[CH:19]=[CH:18][CH:17]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 218436401-(2-Aminoethyl)-1H-imidazol-2(3H)-oneHCID 86640495(1-{4-[2-(2-Chloro-5-fluoro-pyrimidin-4-yl)-benzo[b]thiophen-7-yl]-6-fluoro-pyridin-3-yl}-ethyl)-carbamic acid tert-butyl ester

生成物 1

HCID 66997925{1-[6-Fluoro-4-(2-{5-fluoro-2-[2-(2-oxo-2,3-dihydro-imidazol-1-yl)-ethylamino]-pyrimidin-4-yl}-benzo[b]thiophen-7-yl)-pyridin-3-yl]-ethyl}-carbamic acid tert-butyl ester収率 74%

試薬・触媒・溶媒

2
HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
130 °C

実験手順

Combine (1-{4-[2-(2-chloro-5-fluoro-pyrimidin-4-yl)-benzo[b]thiophen-7-yl]-6-fluoro-pyridin-3-yl}-ethyl)-carbamic acid tert-butyl ester (150 mg, 0.3 mmol), 1-(2-amino-ethyl)-1,3-dihydro-imidazol-2-one (70 mg, 0.55 mmol) and triethylamine (80 mg, 0.8 mmol) in N-methylpyrrolidone (1.0 mL) in a pressure tube. Heat the reaction mixture at 130° C. for 1 hour in a microwave reactor and then cool to room temperature. Dilute the reaction mixture with ethyl acetate, and wash with water and saturated aqueous sodium chloride. Separate the organic layer from the aqueous layer and dry over MgSO4. After filtration, evaporate the organic solvent to give the crude. Purify the crude by column chromatography (10% methanol in dichloromethane) to afford the desired product (80 mg, 74%). MS (ES) m/z 538 [M+t-Bu]+, 494 [M-Boc]−, 616 [M+Na]+.

後処理

  1. temperaturecool to room temperature
  2. washwash with water and saturated aqueous sodium chloride
  3. customSeparate the organic layer from the aqueous layer
  4. dry with materialdry over MgSO4
  5. filtrationAfter filtration
  6. customevaporate the organic solvent
  7. customto give the crude
  8. customPurify the crude by column chromatography (10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-a4ac7988124a4502ba37531fa3a2c7d3
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08063212B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート