Triethylamine → 1-(5-Acetyl-4-methylthiazol-2-yl)-3-{1-[2-(4-fluorophenyl)ethyl]-piperidin-3-ylmethyl}urea

HRID 896534Notes

Reaction equation

HRID 896534 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([CH2:16][NH2:17])[CH2:11]2)=[CH:4][CH:3]=1.C1([O:24][C:25](=O)[NH:26][C:27]2[S:28][C:29]([C:33](=[O:35])[CH3:34])=[C:30]([CH3:32])[N:31]=2)C=CC=CC=1.C(N(CC)CC)C>C(#N)C>[C:33]([C:29]1[S:28][C:27]([NH:26][C:25]([NH:17][CH2:16][CH:12]2[CH2:13][CH2:14][CH2:15][N:10]([CH2:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:11]2)=[O:24])=[N:31][C:30]=1[CH3:32])(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10728523C-{1-[2-(4-Fluorophenyl)ethyl]-piperidin-3-yl}methylamineHCID 22259036Phenyl (5-acetyl-4-methyl-1,3-thiazol-2-yl)carbamate

Product 1

HCID 865917181-(5-Acetyl-4-methylthiazol-2-yl)-3-{1-[2-(4-fluorophenyl)ethyl]-piperidin-3-ylmethyl}ureaYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of C-{1-[2-(4-fluorophenyl)ethyl]-piperidin-3-yl}methylamine (25 mg, 106 μmol), (5-Acetyl-4-methylthiazol-2-yl)-carbamic acid phenyl ester (24 mg, 106 μmol) and triethylamine (29 μL, 210 μmol) in acetonitrile (3 mL) was stirred for 18 hours and concentrated. The residue was purified by flash chromatography, eluting with 5% methanol in dichloromethane, to provide an off-white solid (30 mg, 68%). 1H NMR (300 MHz, CD3OD) δ7.21 (m, 2H), 6.98 (t, J=9 Hz, 2H), 3.16 (m, 2H), 3.02 (m, 2H), 2.82 (m, 2H), 2.61 (m, 2H), 2.56 (s, 3H), 2.47 (s, 3H), 2.09 (m, 1H), 1.85 (m, 4H), 1.65 (m, 1H), 1.05 (m, 1H). Mass spec (ES+) m/z 419.2 (M+H+, 100%).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography
  3. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-db85e5d5f54844cea7afdc0958ec6e82
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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