2-Aminopyridine → 6-chloro-8-(pyridin-2-ylamino)-N-(pyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide

HRID 1943453ノート

反応式

HRID 1943453 の反応式
Br[C:2]1[C:3]2[N:4]([C:9]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[O:13])=[CH:10][N:11]=2)[N:5]=[C:6]([Cl:8])[CH:7]=1.ClC1C=C(Cl)C2N(C(C(NC3C=CN=CC=3)=O)=CN=2)N=1.[N:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[NH2:47].CC(C)([O-])C.[K+]>>[Cl:8][C:6]1[CH:7]=[C:2]([NH:47][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][N:41]=2)[C:3]2[N:4]([C:9]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[O:13])=[CH:10][N:11]=2)[N:5]=1

参加物

5

反応物 4

HCID 104392-AminopyridineHCID 23665647Potassium tert-butoxideHCID 596245908-Bromo-6-chloro-N-(pyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamideHCID 596246716,8-Dichloro-N-(pyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide

生成物 1

HCID 596246846-chloro-8-(pyridin-2-ylamino)-N-(pyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide収率 55.5%

実験手順

To a vial was added a mixture of 8-bromo-6-chloro-N-(pyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide and 6,8-dichloro-N-(pyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide 1E (0.316 g, 0.896 mmol) and pyridin-2-amine (0.084 g, 0.896 mmol). The vial was purged with nitrogen, and THF (1 mL) was added. Potassium tert-butoxide (2.69 mL, 2.69 mmol, 1M in THF) was added and the mixture was stirred at room temperature. After 1 h, the reaction was quenched with a few drops of TFA and methanol. The precipitate was filtered and the powder was washed with methanol to provide 6-chloro-8-(pyridin-2-ylamino)-N-(pyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide (0.2952 g, 0.497 mmol, 55.5% yield) as a pink solid.

後処理

  1. additionTo a vial was added
  2. customThe vial was purged with nitrogen, and THF (1 mL)
  3. additionwas added
  4. customthe reaction was quenched with a few drops of TFA and methanol
  5. filtrationThe precipitate was filtered
  6. washthe powder was washed with methanol

出典と根拠

ORDレコード
ord-846a1dfe575a46a89741631bd24203ae
出典データセット
uspto-grants-2013_03
特許番号
US08389527B2

反応ノート

読み込み中…