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Hydrochloric Acid → 3-(1-(4-amino-3-(5-hydroxy-6-(trifluoromethyl)pyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-one

HRID 634511
ノート
印刷プレビュー

反応式

HRID 634511 の反応式
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[O:15][C:16](=[O:30])[C:17]4[C:22]([C:23]=3[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH3:13])[N:9]=[C:10](I)[C:3]=12.C([O:38][C:39]1[CH:40]=[C:41](B(O)O)[CH:42]=[N:43][C:44]=1[C:45]([F:48])([F:47])[F:46])C1C=CC=CC=1.Cl.[H][H]>CC(O)C.[Pd]>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[O:15][C:16](=[O:30])[C:17]4[C:22]([C:23]=3[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH3:13])[N:9]=[C:10]([C:41]3[CH:42]=[N:43][C:44]([C:45]([F:47])([F:48])[F:46])=[C:39]([OH:38])[CH:40]=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 1181310533-(1-(4-Amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-oneHCID 123469151(5-(Benzyloxy)-6-(trifluoromethyl)pyridin-3-yl)boronic acidHCID 178418361HCID 178418361、化合物

生成物 1

HCID 1181314773-(1-(4-amino-3-(5-hydroxy-6-(trifluoromethyl)pyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-one
収率 51.8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 3776Isopropanol溶媒

実験手順

The title compound was made in a similar way as that of example 68, using 3-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-one (intermediate D2a, 100 mg, 0.196 mmol) and (5-(benzyloxy)-6-(trifluoromethyl)pyridin-3-yl)boronic acid (Intermediate G25, 87 mg, 0.295 mmol). The resulting crude material was reacted in 2-Propanol (10 ml) with 1 N aqueous HCl (1 ml), palladium on carbon 5% wet (0.071 mmol) and hydrogen (1 atm). Then, catalyst was filtered off over celite pad and solvent was removed. Target product was purified by purified by C18 flash chromatography (Snap 30 g chromatography ((H2O/ACN)) 95:5+0.1% HCOOH}:{(ACN/H2O) 95:5+HCOOH 0.1%} from 100:0 to 0:100 affording the title compound (20 mg, 0.037 mmol, 51.8% yield) as a white solid.

後処理

  1. filtrationThen, catalyst was filtered off over celite pad and solvent
  2. customwas removed
  3. customTarget product was purified
  4. customby purified by C18 flash chromatography (Snap 30 g chromatography ((H2O/ACN)) 95:5+0.1% HCOOH

出典と根拠

ORDレコード
ord-ddb9066373c94f2ebe2f85a75ef7718a
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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