Triethylamine → HCID 69736268, compound

HRID 896548Notes

Reaction equation

HRID 896548 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]=[CH:32][CH:31]=[C:30]([C:34]3[N:38]([CH3:39])[N:37]=[N:36][N:35]=3)[CH:29]=2)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O>[CH3:39][N:38]1[C:34]([C:30]2[CH:29]=[C:28]([NH:27][C:26]([NH:18][CH2:17][C@H:12]3[C@@H:13]([CH3:16])[CH2:14][CH2:15][N:10]([CH2:9][CH2:8][C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:11]3)=[O:25])[CH:33]=[CH:32][CH:31]=2)=[N:35][N:36]=[N:37]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22252681phenyl 3-(1-methyl-1H-tetraazol-5-yl)phenylcarbamateHCID 69736296HCID 69736296, compound

Product 1

HCID 69736268HCID 69736268, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of cis-1-[2-(4-fluorophenyl)ethyl]-4-methyl-piperidin-3-ylmethylamine (54 mg, 215 μmol) and [3-(1-methyl-1H-tetrazol-5-yl)phenyl]-carbamic acid phenyl ester (64 mg, 215 μmol) in N,N-dimethylformamide (2 mL) was treated with triethylamine (60 μL, 431 μmol). After 18 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, to provide an amorphous solid (73 mg, 75%). 1H NMR (300 MHz, CDCl3) δ7.95 (s, 1H), 7.64 (d, J=7 Hz, 1H), 7.41 (t, J=8 Hz, 1H), 7.29 (m, 1H), 7.11 (m, 2H), 6.97 (t, J=9 Hz, 2H), 4.17 (s, 3H), 3.42 (m, 1H), 3.26 (m, 1H), 3.1-2.5 (m, 8H), 2.1-1.6 (m, 4H), 0.99 (d, J=7 Hz, 3H). Mass spec (AP+) m/z 452.1 (M+H+).

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-1b27264dce3f4a5d80d744f70caa9860
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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