Triethylamine → HCID 10391002, compound

HRID 896571Notes

Reaction equation

HRID 896571 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:13]([CH3:17])([CH3:16])[CH:12]([CH2:18][NH2:19])[CH2:11]2)=[CH:4][CH:3]=1.C1([O:26][C:27](=O)[NH:28][C:29]2[CH:34]=[C:33]([C:35]3[N:39]([CH3:40])[N:38]=[N:37][N:36]=3)[CH:32]=[C:31]([CH2:41][CH3:42])[CH:30]=2)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O>[CH2:41]([C:31]1[CH:30]=[C:29]([NH:28][C:27]([NH:19][CH2:18][CH:12]2[C:13]([CH3:17])([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:26])[CH:34]=[C:33]([C:35]2[N:39]([CH3:40])[N:38]=[N:37][N:36]=2)[CH:32]=1)[CH3:42]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22252693Phenyl 3-ethyl-5-(1-methyl-1H-tetraazol-5-yl)phenylcarbamateHCID 69737865HCID 69737865, compound

Product 1

HCID 10391002HCID 10391002, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[2-(4-fluorophenyl)ethyl]-4,4-dimethyl-piperidin-3-ylmethylamine (53 mg, 199 μmol) and [3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-carbamic acid phenyl ester (50 mg, 199 μmol) in N,N-dimethylformamide (1.0 mL) was treated with triethylamine (55 μL, 398 μmol). After 18 hours, the mixture was concentrated under vacuum. The residue was purified by flash chromatography, eluting with 5% methanol in dichloromethane containing 0.5% aqueous ammonium hydroxide, providing an amorphous solid (50 mg, 50%). 1H NMR (300 MHz, CDCl3) δ8.45 (s, 1H), 7.66 (s, 1H), 7.62 (s, 1H), 7.09 (m, 2H), 7.07 (s, 1H), 6.91 (t, J=9 Hz, 2H), 6.23 (m, 1H), 4.13 (s, 3H), 3.38 (m, 1H), 3.10 (m, 2H), 2.85 (m, 3H), 2.74 (m, 2H), 2.62 (q, J=7 Hz, 2H), 2.45 (m, 1H), 2.32 (m, 1H), 1.8-1.6 (m, 2H), 1.46 (m, 1H), 1.21 (t, J=7 Hz, 3H), 1.02 (s, 3H), 0.88 (s, 3H). Mass spec (ES+) m/z 494.3 (M+H+, 100%).

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. customThe residue was purified by flash chromatography
  3. washeluting with 5% methanol in dichloromethane containing 0.5% aqueous ammonium hydroxide

Sources & evidence

ORD record
ord-97ba4765ffc546bcbcf030c4c2b1b02c
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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