Diisopropylethylamine → HCID 89726475, 화합물

HRID 1777728노트

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HRID 1777728 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][C@H:19]1[CH3:24])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].CCN(C(C)C)C(C)C>CN1C(=O)CCC1.CC(=O)OCC>[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][C@H:19]1[CH3:24])=[O:12])([CH3:17])([CH3:15])[CH3:16]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 10262201tert-Butyl (2R)-2-methylpiperazine-1-carboxylateHCID 40787018Methyl 5-bromo-1,3-thiazole-4-carboxylate

생성물 1

HCID 89726475HCID 89726475, 화합물수율 30.8%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
120 °C

실험 절차

To a solution of methyl 5-bromo-1,3-thiazole-4-carboxylate (3 g) in NMP (30 mL) was added (R)-1-N-Boc-2-methylpiperazine (2.76 g) followed by DIPEA (10.1 mL). The resulting solution was stirred at 120° C. for 1.5 d, at RT over weekend and at 120° C. for 7 h. After cooling down, the reaction mixture was diluted with EA and washed with sat. aq. NaHCO3, 1M HCl and sat. aq NaCl. The aq. phases 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: 0 for 10CV, 0 to 10 over 5CV, 10 for 5CV, 10 to 20 over 5CV, 20 for 5CV, 20 to 30 over 5CV, 30 for 5CV) to afford 1.42 g of yellow oil. LC-MS (B): tR=0.84 min; [M+H]+: 342.08.

후처리

  1. temperatureAfter cooling down
  2. washwashed with sat. aq. NaHCO3, 1M HCl and sat. aq NaCl
  3. extractionThe aq. phases 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: 0 for 10CV, 0 to 10 over 5CV, 10 for 5CV, 10 to 20 over 5CV, 20 for 5CV, 20 to 30 over 5CV, 30 for 5CV)

출처 및 근거

ORD 기록
ord-076e2cae0c914f1b89abd6e200a6f4b8
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266876B2

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