Diisopropylethylamine → SB-649,915

HRID 1295582ノート

反応式

HRID 1295582 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 10296414SB-649,915収率 26.5%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3ff4cc4fcbbb472faba08f618c65d786
出典データセット
uspto-grants-2007_07
特許番号
US07244726B2

反応ノート

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