1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 89726458, 화합물

HRID 1777726노트

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HRID 1777726 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

HCID 89726458HCID 89726458, 화합물수율 51.9%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b1ab0fff90eb4fd1ad6510d135cd6a0d
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266876B2

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