Dimethylformamide → 4-[2-(ethylsulfonyl)ethyl]-N-methylbicyclo[2.2.2]octane-1-carboxamide

HRID 605510Notes

Reaction equation

HRID 605510 reaction equation
C12CC3CC(CC(C3)[CH:2]1[NH:11][C:12]([C:14]13[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])([CH2:18][CH2:19]1)[CH2:16][CH2:15]3)=[O:13])C2.C12CC3CC(CC(C3)C1N)C2.CN(C=O)C.C(N(C(C)C)CC)(C)C>C(#N)C>[CH2:27]([S:24]([CH2:23][CH2:22][C:17]12[CH2:18][CH2:19][C:14]([C:12]([NH:11][CH3:2])=[O:13])([CH2:21][CH2:20]1)[CH2:15][CH2:16]2)(=[O:26])=[O:25])[CH3:28]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 253322-AminoadamantaneHCID 81531DiisopropylethylamineHCID 11502385N-2-adamantyl-4-[2-(ethylsulfonyl)ethyl]bicyclo[2.2.2]octane-1-carboxamide

Product 1

HCID 207550374-[2-(ethylsulfonyl)ethyl]-N-methylbicyclo[2.2.2]octane-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Amide 1-6 was made from acid chloride 1-5 (810 mg, 2.96 mmol) as one member of a 96 compound library, employing the technique of parallel synthesis using the Myriad Core System/nMiniblock. According to the general procedure, 0.10 mmol of each amine (2-adamantylamine for this product) was weighed into the miniblock reaction tubes, and 0.350 ml of dry DMF and 0.55 ml of dry diisopropylethylamine was added to each tube. A 0.25 M solution of the acid chloride in dry acetonitrile was prepared, and 0.400 ml of this solution was dispensed to each tube and the reactions were incubated and stirred overnight under an inert nitrogen atmosphere. The products were purified using a Fraction Lynx HPLC (with detection according to mass spectrum) equipped with a Waters Xterra MS C18 5 um 19×50 nm reverse phase column running a gradient of water/acetonitrile (0.1% TFA). The fractions containing product were concentrated to remove some of the acetonitrile and the lyophilized to provide pure product 4-[2-(ethylsulfonyl)ethyl]-N-methylbicyclo[2.2.2]octane-1-carboxamide 1-6 as a white fluffy amorphous solid.

Workup

  1. customthe technique of parallel synthesis
  2. additionwas added to each tube
  3. customThe products were purified
  4. customequipped with a Waters Xterra MS
  5. additionThe fractions containing product
  6. concentrationwere concentrated
  7. customto remove some of the acetonitrile

Sources & evidence

ORD record
ord-c27bc14c83514484bc79296a5eb267f0
Source dataset
uspto-grants-2011_03
Patent number
US07915252B2

Reaction notes

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