Triethylamine → HCID 86646710, compound

HRID 1809075Notes

Reaction equation

HRID 1809075 reaction equation
[N:1]1([C:11]([C:13]2[CH:17]=[C:16]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[S:15][CH:14]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>ClCCl>[CH3:31][S:32]([N:21]1[CH2:20][CH2:19][CH:18]([C:16]2[S:15][CH:14]=[C:13]([C:11]([N:1]3[C@@H:10]4[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]4)[CH2:4][CH2:3][CH2:2]3)=[O:12])[CH:17]=2)[CH2:23][CH2:22]1)(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86646702cis-(Octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone

Product 1

HCID 86646710HCID 86646710, compoundYield 44.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

cis-(Octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone (CC-033) (0.04 g, 0.12 mmol) was dissolved in dichloromethane (2 mL) and triethylamine (0.37 mmol). Methylsulphonyl chloride (0.25 mmol) was added and the mixture stirred for 2 hours and then the solvent removed by evaporation. The residue 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 (0.022 g). LCMS m/z 411.11 min [M+H]+ RT=10.84 min (Analytical Method 2). 1H NMR (400 MHz, CHCl3-d): δ 7.2 (s, 1H), 6.9 (s, 1H), 4.6 (m, 1H), 3.9-3.6 (m, 3H), 3.1-2.7 (m, 2H), 2.7 (s, 3H), 2.1-1.1 (m, 19H).

Workup

  1. customthe solvent removed by evaporation
  2. customThe residue 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-d682a8f7dacf4078bfe4931107d3fb58
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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