Acetyl chloride → 1-{4-[4-(Azepane-1-carbonyl)-thiophen-2-yl]-3,6-dihydro-2H-pyridin-1-yl}-ethanone

HRID 1809102Notes

Reaction equation

HRID 1809102 reaction equation
[N:1]1([C:8]([C:10]2[CH:14]=[C:13]([C:15]3[CH2:16][CH2:17][NH:18][CH2:19][CH:20]=3)[S:12][CH:11]=2)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:28](Cl)(=[O:30])[CH3:29]>C(Cl)Cl>[N:1]1([C:8]([C:10]2[CH:14]=[C:13]([C:15]3[CH2:16][CH2:17][N:18]([C:28](=[O:30])[CH3:29])[CH2:19][CH:20]=3)[S:12][CH:11]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 59542518Azepan-1-yl-[5-(1,2,3,6-tetrahydro-pyridin-4-yl)-thiophen-3-yl]-methanone

Product 1

HCID 426448311-{4-[4-(Azepane-1-carbonyl)-thiophen-2-yl]-3,6-dihydro-2H-pyridin-1-yl}-ethanoneYield 33.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of azepan-1-yl-[5-(1,2,3,6-tetrahydro-pyridin-4-yl)-thiophen-3-yl]-methanone (0.023 g, 0.08 mmol) in DCM (1 mL) was added triethylamine (0.27 mmol) and acetyl chloride (0.11 mmol). The reaction mixture was stirred for 1 hour, and then the solvent evaporated. The product 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 as a colourless oil (0.009 g). LCMS m/z 333.11 [M+H]+ RT=8.18 min (Analytical Method 2).

Workup

  1. customthe solvent evaporated
  2. customThe product was purified by HPLC
  3. washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
  4. additionThe fractions containing the desired product
  5. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-568c47a4a71249568d21d93cf97807f7
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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