Water → (5-Ethyl-thiophen-3-yl)-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone

HRID 1809079Notes

Reaction equation

HRID 1809079 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[CH2:13]([C:15]1[S:19][CH:18]=[C:17]([C:20]([OH:22])=O)[CH:16]=1)[CH3:14].[CH3:23][C:24]12[CH2:31][CH:28]([NH:29][CH2:30]1)[CH2:27][C:26]([CH3:33])([CH3:32])[CH2:25]2.O>C(Cl)Cl>[CH2:13]([C:15]1[S:19][CH:18]=[C:17]([C:20]([N:29]2[CH2:30][C:24]3([CH3:23])[CH2:31][CH:28]2[CH2:27][C:26]([CH3:33])([CH3:32])[CH2:25]3)=[O:22])[CH:16]=1)[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 1037871,3,3-Trimethyl-6-azabicyclo(3.2.1)octaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 35615485-Ethylthiophene-3-carboxylic acid

Product 1

HCID 59542598(5-Ethyl-thiophen-3-yl)-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanoneYield 61.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.06 g; 1.2 eq) was added to a solution of 5-ethyl-thiophene-3-carboxylic acid (0.04 g; 1 eq.) in DCM (1 mL/100 mg of starting material). This mixture was stirred at room temperature for 5 minutes, then 1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane (0.043 g; 1.1 eq.) added and the mixture allowed to stir for 18 hours. Water (1 mL/100 mg of starting material) was then added and the organic layer separated, dried and evaporated to give the crude product which was purified by column chromatography (EtOAc/iso-hexane) to give the title compound (0.046 g). LCMS m/z 292 [M+H]+ RT=4.28 min (Analytical Method 3).

Workup

  1. stirringto stir for 18 hours
  2. customthe organic layer separated
  3. customdried
  4. customevaporated
  5. customto give the crude product which
  6. customwas purified by column chromatography (EtOAc/iso-hexane)

Sources & evidence

ORD record
ord-53f1d381fba942b98c43c274bef4b150
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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