1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 89726458、化合物

HRID 1777726ノート

反応式

HRID 1777726 の反応式
Br[C:2]1[S:6][CH:5]=[N:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].[C:11]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C1CCN2C(=NCCC2)CC1>CC#N.CC(=O)OCC.O>[C:14]([O:13][C:11]([N:18]1[CH2:23][CH2:22][N:21]([C:2]2[S:6][CH:5]=[N:4][C:3]=2[C:7]([O:9][CH3:10])=[O:8])[CH2:20][CH2:19]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

参加物

7

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 40787018Methyl 5-bromo-1,3-thiazole-4-carboxylate

生成物 1

HCID 89726458HCID 89726458、化合物収率 51.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a solution of methyl 5-bromo-1,3-thiazole-4-carboxylate (10 g) in MeCN (120 mL) was added 1-Boc-piperazine (8.56 g) followed by DBU (10.1 mL). The resulting solution was stirred at 80° C. for 5 h. The reaction mixture was diluted with EA and water. The layers were separated and the org. phase was further washed with water. The combined aq. layers were extracted with EA. The combined org. layers were dried over Na2SO4, filtrated off and evaporated in vacuo. The crude was purified by CC (Biotage, SNAP 100 g cartridge, solvent A: Hept; solvent B: EA; gradient in % B: 10 for 2CV, 10 to 50 over 12CV, 50 for 3CV) to afford 7.65 g of yellow oil. LC-MS (B): tR=0.79 min; [M+H]+: 328.37.

後処理

  1. customThe layers were separated
  2. washphase was further washed with water
  3. extractionThe combined aq. layers were extracted with EA
  4. dry with materiallayers were dried over Na2SO4
  5. filtrationfiltrated off
  6. customevaporated in vacuo
  7. customThe crude was purified by CC (Biotage, SNAP 100 g cartridge, solvent A: Hept; solvent B: EA; gradient in % B: 10 for 2CV, 10 to 50 over 12CV, 50 for 3CV)

出典と根拠

ORDレコード
ord-b1ab0fff90eb4fd1ad6510d135cd6a0d
出典データセット
uspto-grants-2016_02
特許番号
US09266876B2

反応ノート

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