Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → 4-fluoro-5-(3-fluoro-2-methyl-5-(3-(pyridin-2-yl)oxetan-3-ylcarbamoyl)phenyl)-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide

HRID 1892556ノート

反応式

HRID 1892556 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:12]2[CH:13]=[CH:14][C:15]3[O:19][C:18]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)=[C:17]([C:27](=[O:30])[NH:28][CH3:29])[C:16]=3[C:31]=2[F:32])[C:10]=1[CH3:11])[C:5](O)=[O:6].Cl.Cl.[N:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41]1([NH2:45])[CH2:44][O:43][CH2:42]1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[F:32][C:31]1[C:16]2[C:17]([C:27]([NH:28][CH3:29])=[O:30])=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[O:19][C:15]=2[CH:14]=[CH:13][C:12]=1[C:9]1[CH:8]=[C:4]([C:5](=[O:6])[NH:45][C:41]2([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][N:35]=3)[CH2:42][O:43][CH2:44]2)[CH:3]=[C:2]([F:1])[C:10]=1[CH3:11]

参加物

6

反応物 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 584729003-Fluoro-5-(4-fluoro-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methylbenzoic acidHCID 679580363-(pyridin-2-yl)oxetan-3-amine 2HCl

生成物 1

HCID 573367934-fluoro-5-(3-fluoro-2-methyl-5-(3-(pyridin-2-yl)oxetan-3-ylcarbamoyl)phenyl)-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 3-fluoro-5-(4-fluoro-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methylbenzoic acid (0.050 g, 0.114 mmol, 1.0 eq) and 3-(pyridin-2-yl)oxetan-3-amine 2HCl (0.03 g, 0.134 mmol, 1.2 eq) in DMF at 0° C. was added TEA (0.15 ml, 1.08 mmol, 9 eq) and BOP reagent (0.06 g, 0.136 mmol, 1.2 eq). The reaction mixture was stirred as rt overnight. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 filtered and the filtrate concentrated. The crude product was purified by preparative HPLC. Yield: 0.010 g (15.3%).

後処理

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. customThe crude product was purified by preparative HPLC

出典と根拠

ORDレコード
ord-cf7269d411c240a6bbaaa74969aee0b1
出典データセット
uspto-grants-2013_08
特許番号
US08507683B2

反応ノート

読み込み中…