Diisopropylethylamine → 4-benzyloxy-N-[3-tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-2-fluoro-benzamide

HRID 2390875ノート

反応式

HRID 2390875 の反応式
[C:1]([C:5]1[C:6]([O:20][CH3:21])=[C:7]([NH2:19])[CH:8]=[C:9]([C:11]2[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:22]([O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][C:31]=1F)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.[F:57][P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>O.CN(C=O)C>[CH2:22]([O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH:19][C:7]2[CH:8]=[C:9]([C:11]3[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=3)[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:6]=2[O:20][CH3:21])=[O:35])=[C:32]([F:57])[CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 187575074-Benzyloxy-3-fluorobenzoic acidHCID 670698823-Tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenylamine

生成物 1

HCID 670699134-benzyloxy-N-[3-tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-2-fluoro-benzamide収率 85%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

step 1—A solution of 100 (100 mg, 0.349 mmol, 4-benzyloxy-3-fluoro-benzoic acid (86 mg, 0.349 mmol), HATU (146 mg, 0.384 mmol, DIPEA (0.122 mL, 0.698 mmol), and DMF (3 mL) is stirred at 50° under Ar overnight. The reaction was cooled, diluted with H2O and extracted with EtOAc. The combined extracts were washed with H2O, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 eluting with 20% EtOAc/hexane to afford 0.125 g (85%) of 4-benzyloxy-N-[3-tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-2-fluoro-benzamide (322) which could be recrystallized from EtOAc.

後処理

  1. temperatureThe reaction was cooled
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with H2O
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by SiO2 eluting with 20% EtOAc/hexane

出典と根拠

ORDレコード
ord-320bc3aaa98b474dae8c6d199fa38c53
出典データセット
uspto-grants-2012_09
特許番号
US08273773B2

反応ノート

読み込み中…