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Water → 4-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(2-(pyridin-4-yl)ethyl)benzamide

HRID 1410029
ノート
印刷プレビュー

反応式

HRID 1410029 の反応式
Cl[C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.[N:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][NH:30][C:31](=[O:47])[C:32]2[CH:37]=[CH:36][C:35](B3OC(C)(C)C(C)(C)O3)=[CH:34][CH:33]=2)=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:21][O:20][C:14]1[CH:13]=[C:12]([NH:11][C:4]2[C:5]3[N:10]=[CH:9][S:8][C:6]=3[N:7]=[C:2]([C:35]3[CH:36]=[CH:37][C:32]([C:31]([NH:30][CH2:29][CH2:28][C:25]4[CH:26]=[CH:27][N:22]=[CH:23][CH:24]=4)=[O:47])=[CH:33][CH:34]=3)[N:3]=2)[CH:17]=[CH:16][C:15]=1[O:18][CH3:19]
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 962WaterHCID 10340Sodium CarbonateHCID 68379398N-(2-(pyridin-4-yl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 715341855-chloro-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine

生成物 1

HCID 665491384-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(2-(pyridin-4-yl)ethyl)benzamide収率 31.5%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

To a stirred solution of 5-chloro-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine (100 mg, 0.31 mmol) and N-(2-(pyridin-4-yl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (140 mg, 0.4 mmol) in 25 mL of 1,4-dioxane were added Na2CO3 (64 mg, 0.6 mmol) and 3 mL of water at room temperature. Then the mixture was degassed with nitrogen for 15 minutes. Pd(PPh3)4 (20 mg, 0.017 mmol) was added in one portion and the reaction mixture was stirred at reflux for 16 hours under nitrogen. The solvent was evaporated and the residue was purified by silica gel chromatography (200-300 mesh, eluting with EtOAc) to give 4-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(2-(pyridin-4-yl)ethyl)benzamide (50 mg, 31%) as a yellow sold. 1H NMR (300 MHz, DMSO): δ 10.15 (s, 1H), 9.37 (s, 1H), 8.68 (t, 1H, J=5.3 Hz), 8.46-8.42 (m, 4H), 7.94-7.91 (m, 2H), 7.81 (d, 1H, J=2.7 Hz), 7.52-7.47 (m, 1H), 7.27-7.26 (m, 2H), 7.00 (d, 1H, J=8.7 Hz), 4.02 (s, 3H), 4.00 (s, 3H), 3.58-3.52 (m, 2H), 2.89 (t, 2H, J=7.0 Hz). LC-MS: 513 [M+H]+, 511 [M−H]−, tR=1.32 min. HPLC: 97.72% at 214 nm, 96.31% at 254 nm, tR=4.19 min.

後処理

  1. customThen the mixture was degassed with nitrogen for 15 minutes
  2. temperatureat reflux for 16 hours under nitrogen
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel chromatography (200-300 mesh, eluting with EtOAc)

出典と根拠

ORDレコード
ord-600ae5f4ca7349c6be5e423f5f112ffd
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08921383B2

反応ノート

読み込み中…

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