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Triethylamine → 4-fluoro-2-(4-fluorophenyl)-N-methyl-5-(2-methyl-5-(3-(pyrimidin-2-yl)oxetan-3-ylcarbamoyl)phenyl)benzofuran-3-carboxamide

HRID 1892561
ノート
印刷プレビュー

反応式

HRID 1892561 の反応式
[F:1][C:2]1[C:7]2[C:8]([C:18](=[O:21])[NH:19][CH3:20])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[CH3:31])[C:25](O)=[O:26].Cl.[N:33]1[CH:38]=[CH:37][CH:36]=[N:35][C:34]=1[C:39]1([NH2:43])[CH2:42][O:41][CH2:40]1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O>[F:1][C:2]1[C:7]2[C:8]([C:18]([NH:19][CH3:20])=[O:21])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[C:22]1[CH:23]=[C:24]([C:25](=[O:26])[NH:43][C:39]2([C:34]3[N:35]=[CH:36][CH:37]=[CH:38][N:33]=3)[CH2:42][O:41][CH2:40]2)[CH:28]=[CH:29][C:30]=1[CH3:31]
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 4

HCID 8471TriethylamineHCID 9886HexafluorophosphateHCID 592756803-(4-Fluoro-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methylbenzoic acidHCID 679578123-(Pyrimidin-2-yl)oxetan-3-amine hydrochloride

生成物 1

HCID 679585654-fluoro-2-(4-fluorophenyl)-N-methyl-5-(2-methyl-5-(3-(pyrimidin-2-yl)oxetan-3-ylcarbamoyl)phenyl)benzofuran-3-carboxamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a yellow solution mixture of 3-(4-fluoro-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methylbenzoic acid (30 mg, 0.071 mmol) and 3-(pyrimidin-2-yl)oxetan-3-amine hydrochloride (16 mg, 0.085 mmol) in DMF (1 ml) in a 25 ml round-bottomed flask was added benzotriazo-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP) (50 mg, 0.096 mmol), followed by triethylamine (TEA) (0.1 ml, 0.717 mmol), and the reaction mixture stirred for overnight. Ice cooled water was added to the reaction mixture, which was then stirred for 10-15 min. at 0° C. Precipitation was observed. The solid was collected by filtration, washed with cold water, and then dissolved in dichloromethane. The organic was dried over Na2SO4, filtered and concentrated. The crude product was purified by preparative HPLC. Yield (12 mg, 30%).

後処理

  1. additionwas added to the reaction mixture, which
  2. stirringwas then stirred for 10-15 min. at 0° C
  3. customPrecipitation
  4. filtrationThe solid was collected by filtration
  5. washwashed with cold water
  6. dissolutiondissolved in dichloromethane
  7. dry with materialThe organic was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by preparative HPLC
  11. customYield (12 mg, 30%)

出典と根拠

ORDレコード
ord-3c7f8ccfa2904dbd9722b5bc22a39b5b
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08507683B2

反応ノート

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