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

HRID 896546Notes

Reaction equation

HRID 896546 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][C@@H:13]([CH3:16])[C@H:12]([CH2:17][NH2:18])[CH2:11]2)=[CH:4][CH:3]=1.C1([O:25][C:26](=O)[NH:27][C:28]2[CH:33]=[C:32]([C:34]3[N:38]([CH3:39])[N:37]=[N:36][N:35]=3)[CH:31]=[C:30]([CH2:40][CH3:41])[CH:29]=2)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O>[CH2:40]([C:30]1[CH:29]=[C:28]([NH:27][C:26]([NH:18][CH2:17][C@H:12]2[C@H:13]([CH3:16])[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:25])[CH:33]=[C:32]([C:34]2[N:38]([CH3:39])[N:37]=[N:36][N:35]=2)[CH:31]=1)[CH3:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22252693Phenyl 3-ethyl-5-(1-methyl-1H-tetraazol-5-yl)phenylcarbamateHCID 69738210trans-1-[2-(4-Fluorophenyl)ethyl]-4-methyl-piperidin-3-ylmethylamine

Product 1

HCID 103678411-[3-Ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-3-{trans-1-[2-(4-fluorophenyl)-ethyl]-4-methylpiperidin-3-ylmethyl}-ureaYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of trans-1-[2-(4-fluorophenyl)ethyl]-4-methyl-piperidin-3-ylmethylamine (12 mg, 46 μmol) and [3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-carbamic acid phenyl ester (15 mg, 46 μmol) in N,N-dimethylformamide (0.5 mL) was treated with triethylamine (13 μL, 93 μmol). After 23 hours, the mixture was concentrated under vacuum. The residue was purified by flash chromatography, eluting with 3% methanol in dichloromethane containing 0.3% aqueous ammonium hydroxide, provided an amorphous solid (19 mg, 86%). 1H NMR (300 MHz, CDCl3) δ7.71 (s, 1H), 7.64 (s, 1H), 7.11 (m, 3H), 6.91 (t, J=9 Hz, 2H), 4.17 (s, 3H), 3.6-3.3 (m, 3H), 3.2-2.9 (m, 6H), 2.66 (q, J=7 Hz, 2H), 2.50 (m, 1H), 1.9-1.7 (m, 3H), 1.42 (m, 1H), 1.24 (t, J=7 Hz, 3H), 1.01 (d, J=7 Hz, 3H). Mass spec (ES+) m/z 480.4 (M+H+, 100%).

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. customThe residue was purified by flash chromatography
  3. washeluting with 3% methanol in dichloromethane containing 0.3% aqueous ammonium hydroxide

Sources & evidence

ORD record
ord-2c679ad5ceb14bfdaa6d40028d7b07b6
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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