Hexahydro-1,4-diazepine → 1-[(6-Chloropyridin-3-yl)carbonyl]-1,4-diazepane

HRID 404544

反応式

HRID 404544 の反応式
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:8][C:9]1[CH:19]=[CH:18][C:12]([C:13](OCC)=[O:14])=[CH:11][N:10]=1.C([Li])CCCCC.CC([O-])=O.[Na+].CC(O)=O.C([O-])(=O)C.[Na+]>C1COCC1.O.C(O)(=O)C>[Cl:8][C:9]1[N:10]=[CH:11][C:12]([C:13]([N:1]2[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[O:14])=[CH:18][CH:19]=1

参加物

9

反応物 5

HCID 68163Hexahydro-1,4-diazepineHCID 517045Sodium AcetateHCID 2799611Ethyl 6-chloronicotinateHCID 23662384Sodium DiacetateHCID 178506865HCID 178506865、化合物

生成物 1

HCID 509999191-[(6-Chloropyridin-3-yl)carbonyl]-1,4-diazepane

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
20 °C

実験手順

A solution of homopiperazine (385.62 g, 3.85 mol) in THF (3.9 L) was cooled to an internal temperature of 0° C. and ethyl 6-chloronicotinate (285.82 g, 1.54 mol) was added in THF (0.57 L) over 5 min. After stirring for 10 minutes, n-hexyl lithium (2.3 M in hexane, 335 mL, 0.77 mol) was added to the resulting mixture, over 40 min. The resulting mixture was stirred for 2 h at 0° C., then warmed to 20° C. over 1 h. After an additional 15 h at 20° C., the resulting mixture was treated with 1M NaOAc/HOAc buffer (5 L) (prepared by diluting 47.35 g of sodium acetate and 253.2 mL of acetic acid with water to a total volume of 5 L).

後処理

  1. stirringThe resulting mixture was stirred for 2 h at 0° C.
  2. waitAfter an additional 15 h at 20° C.
  3. customprepared

出典と根拠

ORDレコード
ord-9aa9b603fd9940b2a0eba66ac817f0d4
出典データセット
uspto-grants-2014_06
特許番号
US08748596B2

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