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4-Cyclopropylbenzoyl chloride → 4-{4-[3-(4-Cyclopropyl-benzoylamino)-4-fluoro-phenyl]-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamide

HRID 589493
ノート
印刷プレビュー

反応式

HRID 589493 の反応式
[CH3:1][N:2]([CH3:28])[C:3]([N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[NH:27][C:14]3[N:15]=[CH:16][N:17]=[C:18]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[C:21]([NH2:26])[CH:20]=4)[C:13]=3[CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[CH:29]1([C:32]2[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=2)[CH2:31][CH2:30]1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH3:1][N:2]([CH3:28])[C:3]([N:5]1[CH2:6][CH:7]=[C:8]([C:11]2[NH:27][C:14]3[N:15]=[CH:16][N:17]=[C:18]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[C:21]([NH:26][C:36](=[O:37])[C:35]5[CH:39]=[CH:40][C:32]([CH:29]6[CH2:31][CH2:30]6)=[CH:33][CH:34]=5)[CH:20]=4)[C:13]=3[CH:12]=2)[CH2:9][CH2:10]1)=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 441909384-Cyclopropylbenzoyl chlorideHCID 867309864-[4-(3-Amino-4-fluoro-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamide

生成物 1

HCID 712307634-{4-[3-(4-Cyclopropyl-benzoylamino)-4-fluoro-phenyl]-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒
HCID 1049
Pyridine
溶媒

実験手順

A mixture of Intermediate 10 (80 mg, 0.210 mmol), 4-cyclopropyl-benzoyl chloride (J. Med. Chem., 52(14), 4329-4337; 2009) (76 mg, 0.421 mmol), and DMAP (2.6 mg, 0.021 mmol) in pyridine (2 ml) was stirred at r.t. overnight. The mixture was evaporated to dryness, then sat. aqueous NaHCO3 was added, and the mixture was extracted with DCM. The organic layer was dried, filtered, and evaporated to dryness. The residue was purified by flash chromatography (silica gel, EtOAc/MeOH/NH3 gradient) to obtain Example 20.

後処理

  1. customThe mixture was evaporated to dryness
  2. additionsat. aqueous NaHCO3 was added
  3. extractionthe mixture was extracted with DCM
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography (silica gel, EtOAc/MeOH/NH3 gradient)
  8. customto obtain Example 20

出典と根拠

ORDレコード
ord-b2fe64dfa8b74ed9b5ba63e21ce70571
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09233111B2

反応ノート

読み込み中…

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