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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
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HRID 634490 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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

생성물 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
수율 61.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 86621318Acetonitrile water formic acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c254c741618c42deabc3a2be90121e41
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09321776B2

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