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Water → dimethyl 2,2'-({2-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]ethyl}imino)diacetate

HRID 1402547
ノート
印刷プレビュー

反応式

HRID 1402547 の反応式
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[C:16]([O:18][C:19]3[CH:24]=[C:23]([C:25]([NH:27][C:28]4[CH:33]=[C:32]([CH3:34])[CH:31]=[CH:30][C:29]=4[F:35])=[O:26])[CH:22]=[CH:21][C:20]=3[F:36])[CH:15]=[CH:14][N:13]=2)[NH:9][CH:8]=1)=[O:6].C(N([CH2:44][CH3:45])C(C)C)(C)C.Br[CH2:47][C:48]([O:50][CH3:51])=[O:49].[OH2:52].CN([CH:56]=[O:57])C>>[F:36][C:20]1[CH:21]=[CH:22][C:23]([C:25]([NH:27][C:28]2[CH:33]=[C:32]([CH3:34])[CH:31]=[CH:30][C:29]=2[F:35])=[O:26])=[CH:24][C:19]=1[O:18][C:16]1[CH:15]=[CH:14][N:13]=[C:12]([C:10]2[NH:9][CH:8]=[C:7]([C:5]([NH:4][CH2:3][CH2:2][N:1]([CH2:45][C:44]([O:57][CH3:56])=[O:52])[CH2:47][C:48]([O:50][CH3:51])=[O:49])=[O:6])[CH:11]=2)[CH:17]=1
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 5

HCID 962WaterHCID 6228DimethylformamideHCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 71293631N-(2-aminoethyl)-5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrole-3-carboxamide

生成物 1

HCID 71293510
dimethyl 2,2'-({2-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]ethyl}imino)diacetate

反応条件

温度
55 °C

実験手順

To a stirred solution of N-(2-aminoethyl)-5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrole-3-carboxamide (100 mg, 0.20 mmol) and N,N-diisopropylethylamine (129 mg, 1.0 mmol) in 10 ml of anhydrous DMF was added methyl bromoacetate (77 mg, 0.50 mmol). The mixture was heated at 55° C. for 30 minutes and poured into 100 ml of water with vigorous stirring. The precipitates were filtered and dried in vacuo to give the crude, which was purified by silica gel chromatography eluting with 2-3% of MeOH in CHCl3 to afford dimethyl 2,2′-({2-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]ethyl}imino)diacetate as off-white solid. Yield: 80 mg, 62%.

後処理

  1. filtrationThe precipitates were filtered
  2. customdried in vacuo
  3. customto give the crude, which
  4. customwas purified by silica gel chromatography
  5. washeluting with 2-3% of MeOH in CHCl3

出典と根拠

ORDレコード
ord-66d0f3ca36f14e9ca0b44c25e4618d0c
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08906944B2

反応ノート

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