Sodium Carbonate → HCID 178427348、化合物

HRID 75040

反応式

HRID 75040 の反応式
[C:1]([O:5][C:6]([NH:8][C:9](=[N:26]C(=O)OC(C)(C)C)[NH:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([NH:17][C:18]2[C:23]([F:24])=[CH:22][N:21]=[C:20](Cl)[N:19]=2)[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:34][C:35]1[CH:36]=[C:37]2[C:43](B3OC(C)(C)C(C)(C)O3)=[CH:42][N:41]([S:53]([C:56]3[CH:61]=[CH:60][C:59]([CH3:62])=[CH:58][CH:57]=3)(=[O:55])=[O:54])[C:38]2=[N:39][CH:40]=1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[F:24][C:23]1[C:18]([NH:17][C@H:13]2[CH2:14][CH2:15][CH2:16][C@@H:11]([NH:10][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[NH:26])[CH2:12]2)=[N:19][C:20]([C:43]2[C:37]3[C:38](=[N:39][CH:40]=[C:35]([F:34])[CH:36]=3)[N:41]([S:53]([C:56]3[CH:61]=[CH:60][C:59]([CH3:62])=[CH:58][CH:57]=3)(=[O:54])=[O:55])[CH:42]=2)=[N:21][CH:22]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 672856905-fluoro-1-((4-methylphenyl)sulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 178454306HCID 178454306、化合物

生成物 1

HCID 178427348HCID 178427348、化合物

試薬・触媒・溶媒 2

HCID 15220664Palladium--triphenylphosphane (1/1)触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
120 °C

実験手順

Degassed a solution of (Z)-tert-butyl (tert-butoxycarbonylamino) ((1R,3S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexylamino) methylenecarbamate, 70b, (0.200 g, 0.411 mmol), 5-fluoro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine, 44a, (0.205 g, 0.493 mmol) and Na2CO3 (0.616 mL of 2M solution, 1.232 mmol) in dimethoxyethane (15 mL) for 30 min. To the mixture was added palladium triphenylphosphane (0.023 g, 0.021 mmol) and the reaction mixture was heated in a pressure tube at 120° C. for 45 min. The reaction mixture was filtered through a pad of celite and the filtrate concentrated in vacuo. Attempted purification of the resulting residue by silica gel chromatography (10% MeOH/CH2Cl2) yielded a mixture containing mostly desired product that was used without further purification: LCMS RT=2.30 (M+H) 641.02.

後処理

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate concentrated in vacuo
  3. customAttempted purification of the resulting residue by silica gel chromatography (10% MeOH/CH2Cl2)
  4. customyielded a mixture

出典と根拠

ORDレコード
ord-b8ffd87addd14b6f96c8bf97d1460c3f
出典データセット
uspto-grants-2014_09
特許番号
US08829007B2

関連ノート

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