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 2229322ノート

反応式

HRID 2229322 の反応式
[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

参加物

6

反応物 4

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

生成物 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-one収率 50%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-e91951156de448c4ad94fadd4f430e18
出典データセット
uspto-grants-2002_07
特許番号
US06420359B1

反応ノート

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