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Hydrochloric Acid → 3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(5-(piperazin-1-ylmethyl)thiophen-2-yl)-1H-isochromen-1-one dihydrochloride

HRID 634490
ノート
印刷プレビュー

反応式

HRID 634490 の反応式
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:20]([C:22]3[O:23][C:24](=[O:54])[C:25]4[C:30]([C:31]=3[C:32]3[S:36][C:35]([CH2:37][N:38]5[CH2:43][CH2:42][N:41](C(OCC6C=CC=CC=6)=O)[CH2:40][CH2:39]5)=[CH:34][CH:33]=3)=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH3:21])[N:9]=[C:10]([C:11]3[CH:16]=[C:15]([O:17]C)[CH:14]=[C:13]([F:19])[CH:12]=3)[C:3]=12.BrB(Br)Br.CO.[ClH:61]>ClCCl.CC#N.O.C(O)=O>[ClH:61].[ClH:61].[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:20]([C:22]3[O:23][C:24](=[O:54])[C:25]4[C:30]([C:31]=3[C:32]3[S:36][C:35]([CH2:37][N:38]5[CH2:39][CH2:40][NH:41][CH2:42][CH2:43]5)=[CH:34][CH:33]=3)=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH3:21])[N:9]=[C:10]([C:11]3[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]([F:19])[CH:12]=3)[C:3]=12
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 313Hydrochloric AcidHCID 887MethanolHCID 25134Boron tribromideHCID 118131178benzyl 4-((5-(3-(1-(4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)thiophen-2-yl)methyl)piperazine-1-carboxylate

生成物 1

HCID 118131492
3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(5-(piperazin-1-ylmethyl)thiophen-2-yl)-1H-isochromen-1-one dihydrochloride
収率 61.4%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 86621318Acetonitrile water formic acid溶媒

実験手順

In a 250 ml round bottomed flask equipped with a magnetic stirrer benzyl 4-((5-(3-(1-(4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)thiophen-2-yl)methyl)piperazine-1-carboxylate (460 mg, 0.617 mmol) was suspended in 20 ml of dry dichloromethane then 1M tribromoborane in DCM (5 ml) was added and the mixture was stirred overnight at r.t. MeOH (15 ml) and 1M HCl (5 ml) were added and the mixture was stirred for 30 min then organic solvents were evaporated and the crude was purified by reverse phase chromatography eluting with H2O\MeCN\HCOOH 95:5:0.1% and MeCN\H2O\HCOOH 95:5:0.1%, to give the title compound (254 mg, 0.379 mmol, 61.4% yield) as a whitish solid.

後処理

  1. stirringthe mixture was stirred for 30 min
  2. customorganic solvents were evaporated
  3. customthe crude was purified by reverse phase chromatography
  4. washeluting with H2O\MeCN\HCOOH 95:5

出典と根拠

ORDレコード
ord-c254c741618c42deabc3a2be90121e41
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09321776B2

反応ノート

読み込み中…

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