Hydrochloric Acid → Azd-8330

HRID 2068926ノート

反応式

HRID 2068926 の反応式
C([O:3][CH2:4][CH2:5][O:6][NH:7][C:8]([C:10]1[CH:15]=[C:14]([CH3:16])[C:13](=[O:17])[N:12]([CH3:18])[C:11]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=1[F:27])=[O:9])=C.Cl.[OH-].[Na+].C(C(C)=O)C(C)C>O1CCCC1.C(OCC)(=O)C>[F:27][C:21]1[CH:22]=[C:23]([I:26])[CH:24]=[CH:25][C:20]=1[NH:19][C:11]1[N:12]([CH3:18])[C:13](=[O:17])[C:14]([CH3:16])=[CH:15][C:10]=1[C:8]([NH:7][O:6][CH2:5][CH2:4][OH:3])=[O:9]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 7909Methyl Isobutyl KetoneHCID 14798Sodium HydroxideHCID 574691682-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-N-(2-(vinyloxy)ethoxy)-1,6-dihydropyridine-3-carboxamide

生成物 1

HCID 16666708Azd-8330

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

A mixture of 2-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (2-vinyloxy-ethoxy)-amide (500 mg, 915 μmol) and hydrogen chloride (1 mL) in tetrahydrofuran (5 mL) was stirred overnight. Sodium hydroxide (1M, 2.00 mL) was then added, and after a further 10 minutes methyl isobutyl ketone (3 mL) and ethyl acetate (3 mL) were added to the mixture. The layers were separated and the organic solution was washed with 50% brine (4 mL), then evaporated (approximately half the material was lost by spillage). The residue was taken up in methyl isobutyl ketone (3 mL) and ethyl acetate (1 mL) and the mixture was heated to reflux. Upon cooling to 50° C. the mixture went cloudy and isohexane (5 mL) was added. This caused solid to crystallize and the mixture was cooled to 20° C., followed by a further addition of isohexane (5 mL). The solid was then filtered, washed with isohexane (1 mL) and dried in a vacuum oven at 40° C., to provide the title compound, 140 mg.

後処理

  1. customThe layers were separated
  2. washthe organic solution was washed with 50% brine (4 mL)
  3. customevaporated (approximately half the material
  4. temperatureethyl acetate (1 mL) and the mixture was heated to reflux
  5. additionwas added
  6. customThis caused solid to crystallize
  7. temperaturethe mixture was cooled to 20° C.
  8. additionfollowed by a further addition of isohexane (5 mL)
  9. filtrationThe solid was then filtered
  10. washwashed with isohexane (1 mL)
  11. customdried in a vacuum oven at 40° C.

出典と根拠

ORDレコード
ord-cb894112e7a64dec81fdb45d9072a6e0
出典データセット
uspto-grants-2012_10
特許番号
US08299076B2

反応ノート

読み込み中…