Diisopropylethylamine → SB-649,915

HRID 1295582노트

반응식

HRID 1295582 반응식
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]3[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=3[CH:19]=2)[CH2:4][CH2:3]1.Br[CH2:21][CH2:22][O:23][C:24]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:25]=1[CH:26]=[CH:27][C:28]([CH3:34])=[N:29]2.C(N(C(C)C)CC)(C)C>C(O)(C)C>[CH3:34][C:28]1[CH:27]=[CH:26][C:25]2[C:30](=[CH:31][CH:32]=[CH:33][C:24]=2[O:23][CH2:22][CH2:21][N:2]2[CH2:7][CH2:6][CH:5]([CH2:8][C:9]3[CH:10]=[CH:11][C:12]4[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=4[CH:19]=3)[CH2:4][CH2:3]2)[N:29]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 117371925-(2-Bromoethoxy)-2-methylquinolineHCID 223266516-(4-piperidinylmethyl)-4H-benzo[1,4]oxazin-3-one hydrochloride

생성물 1

HCID 10296414SB-649,915수율 26.5%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A mixture of 6-(4-piperidinylmethyl)-4H-benzo[1,4]oxazin-3-one hydrochloride (0.10 g, 0.35 mmol), 5-(2-bromoethoxy)-2-methylquinoline (0.11 g, 0.42 mmol), diisopropylethylamine (1 mL) and isopropanol (10 mL) was heated at reflux under argon for 48 h, cooled, then evaporated in vacuo. The residue was partitioned between saturated aqueous NaHCO3 (50 mL) and dichloromethane (3×30 mL) and the combined organic extracts were dried (Na2SO4) and evaporated in vacuo. The resulting oil was purified by chromatography on silica eluting with 50% ethyl acetate-hexane followed by 0–25% methanol-ethyl acetate gradient elution, to give the title compound (0.04 g, 26%) as an oil.

후처리

  1. temperaturewas heated
  2. temperatureat reflux under argon for 48 h
  3. temperaturecooled
  4. customevaporated in vacuo
  5. customThe residue was partitioned between saturated aqueous NaHCO3 (50 mL) and dichloromethane (3×30 mL)
  6. dry with materialthe combined organic extracts were dried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe resulting oil was purified by chromatography on silica eluting with 50% ethyl acetate-hexane
  9. washfollowed by 0–25% methanol-ethyl acetate gradient elution

출처 및 근거

ORD 기록
ord-3ff4cc4fcbbb472faba08f618c65d786
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07244726B2

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