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Sodium Sulfate → (4-[1-(3-Fluoro-benzyl)-1H-indazol-5-ylamino]-pyrrolo[2,1-f][1,2,4]triazin-5-yl}-methanol

HRID 1072092
ノート
印刷プレビュー

反応式

HRID 1072092 の反応式
Br[CH2:2][C:3]1[CH:4]=[CH:5][N:6]2[C:11]=1[C:10](Cl)=[N:9][CH:8]=[N:7]2.C([O-])(O)=O.[Na+].[O-:18]S([O-])(=O)=O.[Na+].[Na+].[F:25][C:26]1[CH:27]=[C:28]([CH:40]=[CH:41][CH:42]=1)[CH2:29][N:30]1[C:38]2[C:33](=[CH:34][C:35]([NH2:39])=[CH:36][CH:37]=2)[CH:32]=[N:31]1>C(#N)C.O>[F:25][C:26]1[CH:27]=[C:28]([CH:40]=[CH:41][CH:42]=1)[CH2:29][N:30]1[C:38]2[C:33](=[CH:34][C:35]([NH:39][C:10]3[C:11]4=[C:3]([CH2:2][OH:18])[CH:4]=[CH:5][N:6]4[N:7]=[CH:8][N:9]=3)=[CH:36][CH:37]=2)[CH:32]=[N:31]1
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 24436Sodium SulfateHCID 516892Sodium Bicarbonate2 回HCID 71470731-(3-Fluorobenzyl)-1H-indazol-5-amineHCID 218743865-(Bromomethyl)-4-chloropyrrolo[2,1-f][1,2,4]triazine

生成物 1

HCID 22390542(4-[1-(3-Fluoro-benzyl)-1H-indazol-5-ylamino]-pyrrolo[2,1-f][1,2,4]triazin-5-yl}-methanol収率 65%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

A mixture of crude 5-bromomethyl-4-chloro-pyrrolo[2,1-f][1,2,4]triazine (3.69 gm, 0.015 moles and NaHCO3 (2.51 gm, 2 equiv) in a mixture of acetonitrile (50 mL) and water (5 mL) was stirred under a N2 atmosphere for 3 days. This was treated with Na2SO4 and then with 1-(3-flurobenzyl)-1H-indazol-5-ylamine (3.24 gm, 0.90 equiv) and NaHCO3 (1 gm) and left stirring for 18 hr at RT. The reaction was filtered and the filter cake was washed with DCM (100 mL). The filtrate was concentrated and silica gel chromatography (elution with 30% EtOAc in hexane) of the residue gave the title compound as a tan solid (3.78 gm, 65% yield): 1H NMR (CDCl3) δ 3.03 (t, J=5.9 Hz, 1H), 4.98 (d, J=5.7 Hz, 2H), 5.55 (s, 2H), 6.76 (d, J=2.7 Hz, 1H), 6.83 (d, J=9.0 Hz, 1H), 6.98-6.90 (m, 3H), 7.43 (d, J=2.5 Hz, 1H), 7.51 (dd, J=2.1, 8.8 Hz, 1H), 7.96 (s, 1H), 8.03 (s, 1H), 8.22 (s, 1H), 9.91 (s, 1H); MS: (M+H+); HPLC Ret Time: 2.38 min (YMC C18 S5, 3.0×50 mm, 4 min gradient, 4 mL/min.

後処理

  1. stirringstirring for 18 hr at RT
  2. filtrationThe reaction was filtered
  3. washthe filter cake was washed with DCM (100 mL)
  4. concentrationThe filtrate was concentrated
  5. washsilica gel chromatography (elution with 30% EtOAc in hexane) of the residue

出典と根拠

ORDレコード
ord-5cd3ebb762a24326966c6cd8c2733dab
出典データセット
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06908916B2

反応ノート

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