Ethanolamine → HCID 131730180, compound

HRID 1809113Notes

Reaction equation

HRID 1809113 reaction equation
[N:1]1([C:11]([C:13]2[CH:17]=[C:16]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[S:15][CH:14]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.Cl[C:25](OC1C=CC([N+]([O-])=O)=CC=1)=[O:26].[NH2:37][CH2:38][CH2:39][OH:40]>C(Cl)Cl>[OH:40][CH2:39][CH2:38][NH:37][C:25]([N:21]1[CH2:20][CH2:19][CH:18]([C:16]2[S:15][CH:14]=[C:13]([C:11]([N:1]3[C@@H:10]4[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]4)[CH2:4][CH2:3][CH2:2]3)=[O:12])[CH:17]=2)[CH2:23][CH2:22]1)=[O:26]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 821294-Nitrophenyl chloroformateHCID 86646702cis-(Octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone

Product 1

HCID 131730180HCID 131730180, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

cis-(octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone (CC-033) (0.095 g, 0.28 mmol) and 4-nitrophenyl chloroformate (0.29 mmol) were dissolved in DCM (4 mL) and TEA (0.3 mmol) and the resulting mixture stirred overnight. The mixture was diluted with DCM (25 mL) and washed with aqueous citric acid (10% w/v) and saturated aqueous sodium hydrogen carbonate and then brine. After drying with magnesium sulphate, the mixture was filtered and the solvent evaporated to give a clear gum. DCM (3 mL) was added together with 2-aminoethanol (0.26 mmol). The mixture was refluxed overnight and then diluted with DCM (10 mL) and washed with aqueous citric acid (10% w/v) and 2M aqueous sodium carbonate and then brine. After drying with magnesium sulphate, the mixture was filtered and the solvent evaporated to give a yellow gum which was purified by HPLC eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound (0.055 g). LCMS m/z 420.30 [M+H]+ RT=8.68 min (Analytical Method 2).

Workup

  1. washwashed with aqueous citric acid (10% w/v) and saturated aqueous sodium hydrogen carbonate
  2. dry with materialAfter drying with magnesium sulphate
  3. filtrationthe mixture was filtered
  4. customthe solvent evaporated
  5. customto give a clear gum
  6. temperatureThe mixture was refluxed overnight
  7. washwashed with aqueous citric acid (10% w/v) and 2M aqueous sodium carbonate
  8. dry with materialAfter drying with magnesium sulphate
  9. filtrationthe mixture was filtered
  10. customthe solvent evaporated
  11. customto give a yellow gum which
  12. customwas purified by HPLC
  13. washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
  14. additionThe fractions containing the desired product
  15. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-a61edb4a8e2b45bfb20941055651703d
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

Loading…