Toluene → 4-{4-[3-(Cyclopropyl-benzoylamino)-5-fluoro-2-methyl-phenyl]-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 589503ノート

反応式

HRID 589503 の反応式
C1([C:4]2[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[CH:6][CH:5]=2)CC1.S(Cl)(Cl)=O.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH:28]=[C:27]([C:30]2[NH:47][C:33]3[N:34]=[CH:35][N:36]=[C:37]([C:38]4[CH:43]=[C:42]([F:44])[CH:41]=[C:40]([NH2:45])[C:39]=4[CH3:46])[C:32]=3[CH:31]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].[C:48]1([CH3:54])C=CC=C[CH:49]=1>N1C=CC=CC=1>[C:17]([O:21][C:22]([N:24]1[CH2:25][CH:26]=[C:27]([C:30]2[NH:47][C:33]3[N:34]=[CH:35][N:36]=[C:37]([C:38]4[CH:43]=[C:42]([F:44])[CH:41]=[C:40]([N:45]([CH:54]5[CH2:48][CH2:49]5)[C:8](=[O:9])[C:7]5[CH:11]=[CH:12][CH:4]=[CH:5][CH:6]=5)[C:39]=4[CH3:46])[C:32]=3[CH:31]=2)[CH2:28][CH2:29]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

参加物

6

反応物 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 2820644-Cyclopropylbenzoic acidHCID 867309964-[4-(3-Amino-5-fluoro-2-methyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 867309954-{4-[3-(Cyclopropyl-benzoylamino)-5-fluoro-2-methyl-phenyl]-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
80 °C

実験手順

To a solution of 4-cyclopropyl benzoic acid (0.58 g, 3.57 mmol) in toluene (2 ml), thionyl chloride (1.29 ml, 17.87 mmol) was added. The mixture was stirred at 80° C. for 2 hours and afterwards evaporated under reduced pressure. The residue was dissolved together with Intermediate 20 (1.0 g, 2.36 mmol) in pyridine (5 ml) and the mixture was stirred at room temperature for 2 hours. Pyridine was evaporated under reduced pressure and the residue was dissolved in DCM and washed with saturated sodium hydrogen carbonate solution and brine (2×). The residue was purified by flash chromatography on silica (cyclohexane to EtOAc) to afford the compound Intermediate 21 as a beige solid.

後処理

  1. customafterwards evaporated under reduced pressure
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. customPyridine was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in DCM
  5. washwashed with saturated sodium hydrogen carbonate solution and brine (2×)
  6. customThe residue was purified by flash chromatography on silica (cyclohexane to EtOAc)

出典と根拠

ORDレコード
ord-199a934346b34359bfe47368f9b1dc0f
出典データセット
uspto-grants-2016_01
特許番号
US09233111B2

反応ノート

読み込み中…