(S)-[(2R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol → HCID 131726431, compound

HRID 604242Notes

Reaction equation

HRID 604242 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].C1CCC(N=C=NC2CCCCC2)CC1.[CH3:31][O:32][C:33]1[CH:34]=[CH:35][C:36]2[N:42]=[CH:41][CH:40]=[C:39]([C@H:43]([OH:54])[C@@H:44]3[N:49]4[CH2:50][C@H:51]([CH:52]=[CH2:53])[CH:46]([CH2:47][CH2:48]4)[CH2:45]3)[C:37]=2[CH:38]=1.CO.ClCCl>CN(C=O)C.CN(C1C=CN=CC=1)C>[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[CH3:31][O:32][C:33]1[CH:34]=[CH:35][C:36]2[N:42]=[CH:41][CH:40]=[C:39]([C@H:43]([OH:54])[C@@H:44]3[N:49]4[CH2:50][C@H:51]([CH:52]=[CH2:53])[CH:46]([CH2:47][CH2:48]4)[CH2:45]3)[C:37]=2[CH:38]=1

Participants

7

Reactant 4

HCID 5953(S)-[(2R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanolHCID 10868DicyclohexylcarbodiimideHCID 83693Boc-L-ValineHCID 21226129Dichloromethane methanol

Product 1

HCID 131726431HCID 131726431, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Boc-Val-OH (2.00 g.,9.26 mmol) and DCC (1.90 g, 9.26 mmol) were dissolved in dry DMF (20 ml) under a nitrogen atmosphere. The mixture was stirred continuously for one hour at 0° C. A solution of quinidine (1.50 g, 4.63 mmol) and DMAP (0.06 g, -0.65 mmol) in DMF (100 ml) was added dropwise to the reaction mixture at 0° C. The reaction mixture was stirred and allowed to warm to room temperature. After 24 hours, the reaction was checked by TLC (1:13 methanol/dichloromethane mixture) and LC-MS analysis, and was found to be complete. The urea derivative was removed by filtration and washed with ethyl acetate. Solvents from the combined filtrate and washing were totally removed under reduced pressure.

Workup

  1. stirringThe reaction mixture was stirred
  2. temperatureto warm to room temperature
  3. waitAfter 24 hours
  4. customThe urea derivative was removed by filtration
  5. washwashed with ethyl acetate
  6. washSolvents from the combined filtrate and washing
  7. customwere totally removed under reduced pressure

Sources & evidence

ORD record
ord-dff6521e87cb4ee9a2456ac56cd10a34
Source dataset
uspto-grants-2011_03
Patent number
US07910553B2

Reaction notes

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