4-[4-(Azepane-1-carbonyl)-thiophen-2-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester → Azepan-1-yl-[5-(1,2,3,6-tetrahydro-pyridin-4-yl)-thiophen-3-yl]-methanone

HRID 1809101Notes

Reaction equation

HRID 1809101 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[S:15][CH:16]=[C:17]([C:19]([N:21]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:20])[CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[N:21]1([C:19]([C:17]2[CH:18]=[C:14]([C:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=3)[S:15][CH:16]=2)=[O:20])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

4

Reactant 1

HCID 595424584-[4-(Azepane-1-carbonyl)-thiophen-2-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59542518Azepan-1-yl-[5-(1,2,3,6-tetrahydro-pyridin-4-yl)-thiophen-3-yl]-methanoneYield 97.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4-[4-(Azepane-1-carbonyl)-thiophen-2-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.094 g) was dissolved in TFA (1 mL) and DCM (1 mL). The mixture was stirred for 1 hour and then the solvent evaporated. The residue was purified using a SCX-2 column. After washing with methanol and acetonitrile, the desired compound was washed from the column with ammonia (2 M in MeOH). Evaporation gave the title compound as a clear colourless oil (0.068 g). LCMS m/z 291.07 [M+H]+ RT=5.14 min (Analytical Method 2).

Workup

  1. customthe solvent evaporated
  2. customThe residue was purified
  3. washAfter washing with methanol and acetonitrile
  4. washthe desired compound was washed from the column with ammonia (2 M in MeOH)
  5. customEvaporation

Sources & evidence

ORD record
ord-4cc303f7320e4856b61e307d943c2c10
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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