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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
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HRID 1072092 반응식
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
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참가 물질

7

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HCID 24436Sodium SulfateHCID 516892Sodium Bicarbonate2회HCID 71470731-(3-Fluorobenzyl)-1H-indazol-5-amineHCID 218743865-(Bromomethyl)-4-chloropyrrolo[2,1-f][1,2,4]triazine

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5cd3ebb762a24326966c6cd8c2733dab
출처 데이터셋
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06908916B2

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