Triethylamine → trans-1-{4-(Benzyl-methylamino)-1-[2-(4-fluorophenyl)-ethyl]-piperidin-3-ylmethyl}-3-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-urea

HRID 896557Notes

Reaction equation

HRID 896557 reaction equation
[NH2:1][CH2:2][C@H:3]1[C@H:8]([N:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:10])[CH2:7][CH2:6][N:5]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:4]1.C1([O:33][C:34](=O)[NH:35][C:36]2[CH:41]=[C:40]([C:42]3[N:46]([CH3:47])[N:45]=[N:44][N:43]=3)[CH:39]=[C:38]([CH2:48][CH3:49])[CH:37]=2)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O>[CH2:11]([N:9]([CH3:10])[C@@H:8]1[CH2:7][CH2:6][N:5]([CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[CH2:4][C@H:3]1[CH2:2][NH:1][C:34]([NH:35][C:36]1[CH:41]=[C:40]([C:42]2[N:46]([CH3:47])[N:45]=[N:44][N:43]=2)[CH:39]=[C:38]([CH2:48][CH3:49])[CH:37]=1)=[O:33])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22252693Phenyl 3-ethyl-5-(1-methyl-1H-tetraazol-5-yl)phenylcarbamateHCID 69736700trans-{3-Aminomethyl-1-[2-(4-fluorophenyl)-ethyl]-piperidin-4-yl}-benzyl-methylamine

Product 1

HCID 10415913trans-1-{4-(Benzyl-methylamino)-1-[2-(4-fluorophenyl)-ethyl]-piperidin-3-ylmethyl}-3-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of trans-{3-aminomethyl-1-[2-(4-fluorophenyl)-ethyl]-piperidin-4-yl}-benzyl-methylamine (96 mg, 270 μmol), [3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-carbamic acid phenyl ester (87 mg, 270 μmol) and triethylamine (75 μL, 540 μmol) in N,N-dimethylformamide (2 mL) was stirred at room temperature for 20 hours. The solvent was removed under vacuum and the residue was dissolved in dichloromethane. The solution was washed with 1.0 N aqueous sodium hydroxide, then with water, and dried over sodium sulfate and concentrated under vacuum. The residue was purified by flash chromatography, eluting with 4% methanol in dichloromethane containing 0.4% (112 mg, 71%). 1H NMR (300 MHz, CDCl3) δ7.68 (s, 1H), 7.39 (m, 6H), 7.20 (s, 1H), 7.15 (m, 2H), 6.97 (t, J=9 Hz, 2H), 4.14 (s, 3H), 3.80 (m, 1H), 3.7-3.4 (m, 2H), 3.3-3.1 (m, 3H), 2.82 (m, 2H), 2.7-2.5 (m, 5H), 2.29 (s, 3H), 2.1-1.6 (m, 7H), 1.20 (t, J=7 Hz, 3H). Mass spec (ES+) m/z 585.6 (M+H+).

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe solution was washed with 1.0 N aqueous sodium hydroxide
  4. dry with materialwith water, and dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash chromatography
  7. washeluting with 4% methanol in dichloromethane containing 0.4% (112 mg, 71%)

Sources & evidence

ORD record
ord-bd6cfbe1c8bd40a5bca0c95fd7785926
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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