Diisopropylethylamine → 1-[6'-chloro-4'-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

HRID 74687

反応式

HRID 74687 の反応式
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:16])[CH2:3][CH2:2]1.[Cl:17][C:18]1[CH:23]=[C:22]([C:24]([N:26]2[C:34]3[C:29](=[CH:30][C:31]([F:35])=[CH:32][CH:33]=3)[CH2:28][CH2:27]2)=[O:25])[CH:21]=[C:20](Cl)[N:19]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:17][C:18]1[N:19]=[C:20]([N:1]2[CH2:2][CH2:3][CH:4]([N:7]3[C:15]4[C:10](=[N:11][CH:12]=[CH:13][CH:14]=4)[NH:9][C:8]3=[O:16])[CH2:5][CH2:6]2)[CH:21]=[C:22]([C:24]([N:26]2[C:34]3[C:29](=[CH:30][C:31]([F:35])=[CH:32][CH:33]=3)[CH2:28][CH2:27]2)=[O:25])[CH:23]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 22293182Bms-973013HCID 58386613HCID 58386613、化合物

生成物 1

HCID 583865681-[6'-chloro-4'-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

0.74 g (3.4 mmol) 1-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one, 1.0 g (3.2 mmol) (2,6-dichloro-pyridin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone and 0.65 mL (3.8 mmol) DIPEA in 10 mL DMF were stirred for 2 h at RT. Then the reaction mixture was evaporated down, the residue was mixed with water and stirred for 30 min at RT. The precipitated solid was suction filtered, stirred with diisopropylether and isopropanol and suction filtered again. After drying the crude product was purified by preparative HPLC-MS. The product-containing fractions were combined and freeze-dried.

後処理

  1. customThen the reaction mixture was evaporated down
  2. additionthe residue was mixed with water
  3. filtrationfiltered
  4. stirringstirred with diisopropylether and isopropanol and suction
  5. filtrationfiltered again
  6. dry with materialAfter drying the crude product
  7. customwas purified by preparative HPLC-MS
  8. customfreeze-dried

出典と根拠

ORDレコード
ord-823ddf6bf1f54c0c800a71b1bba1c675
出典データセット
uspto-grants-2014_09
特許番号
US08829006B2

関連ノート

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