Hydrochloric Acid → Azd-8330

HRID 2068926노트

반응식

HRID 2068926 반응식
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]

참가 물질

7

반응물 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

생성물 1

HCID 16666708Azd-8330

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-cb894112e7a64dec81fdb45d9072a6e0
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299076B2

반응 노트

불러오는 중…