Water → 8-Bromo-2-chloro-5,11-dihydro-11-ethyl-4-methyl-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 2229322노트

반응식

HRID 2229322 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([NH:13][C:14]2[C:15](Cl)=[N:16][C:17]([Cl:21])=[CH:18][C:19]=2[CH3:20])=[O:12])[C:5]([NH:8][CH2:9][CH3:10])=[N:6][CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1COCC1.O>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[N:6][C:5]2[N:8]([CH2:9][CH3:10])[C:15]3[N:16]=[C:17]([Cl:21])[CH:18]=[C:19]([CH3:20])[C:14]=3[NH:13][C:11](=[O:12])[C:4]=2[CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 184666225-Bromo-n-(2,6-dichloro-4-methyl-3-pyridinyl)-2-(ethylamino)-3-pyridinecarboxamide

생성물 1

HCID 184666018-Bromo-2-chloro-5,11-dihydro-11-ethyl-4-methyl-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one수율 50%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A solution of crude 5-bromo-N-(2,6-dichloro4-methyl-3-pyridinyl)-2-(ethylamino)-3-pyridinecarboxamide (77.7 g, mmol) in anhydrous pyridine (1.0 L) was heated to 50° C. A 1 M solution of NaHMDS in THF (418 mL, 418 mmol) was then added dropwise and stirring was continued for an additional 15 min. After cooling to room temperature, water (50 mL) was added and the mixture concentrated to two-thirds volume on a rotary evaporator. The residue was then poured into water (3 L). Filtration gave the title compound (23.44 g) as a tan solid. The filtrate was extracted with EtOAc (3×) and the combined extracts were washed with water and brine then dried (NgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (hexane:EtOAc, 9:1 or CHCl3) to give an additional amount of the title compound (14.06 g, for a total of 37.50 g, 50% yield for 3 steps).

후처리

  1. concentrationthe mixture concentrated to two-thirds volume on a rotary evaporator
  2. additionThe residue was then poured into water (3 L)
  3. filtrationFiltration

출처 및 근거

ORD 기록
ord-e91951156de448c4ad94fadd4f430e18
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06420359B1

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