Cyclobutanone → (6-Chloro-pyridin-3-yl)-(4-cyclobutyl-[1,4]diazepan-1-yl)-methanone

HRID 404546노트

반응식

HRID 404546 반응식
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[C:17]1(=O)[CH2:20][CH2:19][CH2:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClC(Cl)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][N:13]([CH:17]3[CH2:20][CH2:19][CH2:18]3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 14496CyclobutanoneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 509999191-[(6-Chloropyridin-3-yl)carbonyl]-1,4-diazepane

생성물 1

HCID 58076653(6-Chloro-pyridin-3-yl)-(4-cyclobutyl-[1,4]diazepan-1-yl)-methanone

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of (6-chloro-pyridin-3-yl)[1,4]diazepan-1-yl-methanone (255.1 g, 1.06 mol) in dichloroethane (3.0 L) was added cyclobutanone (108.1 mL, 1.45 mol). After a 1 h aging period, sodium triacetoxyborohydride (308.2 g, 1.45 mol) was added in four equal portions over 1.5 h. The resulting mixture was allowed to stir for 20 h, then quenched with 2.5 L of an aqueous solution containing NaOH (141.3 g, 3.53 mol). After stirring for 30 minutes, the layers were separated and the organic dried with magnesium sulfate, filtered, and concentrated to yield the title compound as an oil.

후처리

  1. customquenched with 2.5 L of an aqueous solution
  2. stirringAfter stirring for 30 minutes
  3. customthe layers were separated
  4. dry with materialthe organic dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c4f23b62bd9149b79cfd132d752d3ed9
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748596B2

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