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Acetic Acid → (R)-4-[5-[[2-[[tert-Butyldimethylsilyl)oxy]-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]pentyl]-N-[[1,6-diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]benzamide

HRID 385273
ノート
印刷プレビュー

反応式

HRID 385273 の反応式
[BH3-]C#N.[Na+].[NH2:5][CH2:6][C@@H:7]([C:16]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20](=[O:27])[NH:21]2)[O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[CH2:28]([N:30]1[C:34]2=[N:35][C:36]([CH2:62][CH3:63])=[C:37]([CH2:46][NH:47][C:48](=[O:61])[C:49]3[CH:54]=[CH:53][C:52]([CH2:55][CH2:56][CH2:57][CH2:58][CH:59]=O)=[CH:51][CH:50]=3)[C:38]([NH:39][CH:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)=[C:33]2[CH:32]=[N:31]1)[CH3:29].C(O)(=O)C.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O.O>[Si:9]([O:8][C@H:7]([C:16]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20](=[O:27])[NH:21]2)[CH2:6][NH:5][CH2:59][CH2:58][CH2:57][CH2:56][CH2:55][C:52]1[CH:51]=[CH:50][C:49]([C:48]([NH:47][CH2:46][C:37]2[C:38]([NH:39][CH:40]3[CH2:41][CH2:42][O:43][CH2:44][CH2:45]3)=[C:33]3[CH:32]=[N:31][N:30]([CH2:28][CH3:29])[C:34]3=[N:35][C:36]=2[CH2:62][CH3:63])=[O:61])=[CH:54][CH:53]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 58505298N-[[1,6-Diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]-4-(5-oxopentyl)benzamideHCID 59023604(R)-5-(2-Amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-hydroxyquinolin-2(1H)-one

生成物 1

HCID 66989901
(R)-4-[5-[[2-[[tert-Butyldimethylsilyl)oxy]-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]pentyl]-N-[[1,6-diethyl-4-[(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl]benzamide
収率 48.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

NaCNBH3 (160 mg, 2.55 mmol) was added to a solution of Intermediate 2 (240 mg, 0.61 mmol), Intermediate 36 (250 mg, 0.51 mmol), and acetic acid (0.032 mL, 0.561 mmol) in THF (5 mL). The reaction mixture was stirred at rt for 1 h. H2O (2 mL) was added followed by satd. NaHCO3 solution (20 mL) and EtOAc (100 mL). The organic layer was separated, dried over MgSO4 (s), filtered, and concentrated in vacuo. Purification by column chromatography on silica gel eluting with a gradient of 0-100% DCM-DCM/MeOH/Ammonia (80/20/1) afforded the title compound as a yellow solid (200 mg). ES/MS calcd. for C45H64N7O5Si+ 810.5. found m/z=810.5 (M+H)+.

後処理

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4 (s)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography on silica gel eluting with a gradient of 0-100% DCM-DCM/MeOH/Ammonia (80/20/1)

出典と根拠

ORDレコード
ord-1893edecbe03499791c6acf338fad33a
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08367829B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート