Diisopropylethylamine → SB-649,915

HRID 1295582Notes

Reaction equation

HRID 1295582 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 10296414SB-649,915Yield 26.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3ff4cc4fcbbb472faba08f618c65d786
Source dataset
uspto-grants-2007_07
Patent number
US07244726B2

Reaction notes

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