Acetonitrile → HCID 69416246, compound

HRID 1766404Notes

Reaction equation

HRID 1766404 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C@@H:7]2[CH2:12][CH2:11][CH2:10][N:9]([CH:13]3[CH:20]4[CH:16]([CH2:17][NH:18][CH2:19]4)[CH2:15][CH2:14]3)[CH2:8]2)=[CH:4][CH:3]=1.C1([O:29][C:30](=O)[NH:31][C:32]2[CH:37]=[C:36]([C:38]3[N:42]([CH3:43])[N:41]=[N:40][N:39]=3)[CH:35]=[C:34]([CH2:44][CH3:45])[CH:33]=2)C=CC=CC=1.C(N(CC)CC)C.C(#N)C>C(OCC)(=O)C>[CH2:44]([C:34]1[CH:33]=[C:32]([NH:31][C:30]([N:18]2[CH2:19][CH:20]3[CH:13]([N:9]4[CH2:10][CH2:11][CH2:12][C@@H:7]([CH2:6][C:5]5[CH:4]=[CH:3][C:2]([F:1])=[CH:22][CH:21]=5)[CH2:8]4)[CH2:14][CH2:15][CH:16]3[CH2:17]2)=[O:29])[CH:37]=[C:36]([C:38]2[N:42]([CH3:43])[N:41]=[N:40][N:39]=2)[CH:35]=1)[CH3:45]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 22252693Phenyl 3-ethyl-5-(1-methyl-1H-tetraazol-5-yl)phenylcarbamateHCID 69413841HCID 69413841, compound

Product 1

HCID 69416246HCID 69416246, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (3aRS,4RS,6aSR)-4-[(3S)-3-(4-fluorobenzyl)piperidin-1-yl]octahydrocyclopenta[c]pyrrole (53 mg, 175 μmol), [3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-carbamic acid phenyl ester (56 mg, 175 μmol), triethylamine (49 μL, 350 μmol) and acetonitrile (2 mL) was stirred at room temperature. After 18 hours, the mixture was concentrated to provide a residue. The residue was dissolved in ethyl acetate. The solution was washed with 1.0 N aqueous sodium hydroxide, and was dried over sodium sulfate and concentrated to provide a residue. The residue was purified by flash column chromatography, eluting with 2% methanol/dichloromethane containing 0.2% aqueous ammonia, to provide a tan glass (56 mg, 75%). 1H NMR (300 MHz, CDCl3) δ7.83 (s, 1H), 7.37 (s, 1H), 7.29 (s, 1H), 7.09 (m, 2H), 6.96 (m, 2H), 6.52 (broad s, 1H), 4.22 (s, 3H), 3.61 (m, 2H), 3.5-3.2 (m, 2H), 3.0-2.6 (m, 6H), 2.6-2.4 (m, 3H), 2.0-1.5 (m, 10H), 1.27 (m, 3H), 0.93 (m, 1H). Mass spec (ES+) m/z 532.4 (M+H+, 100%)

Workup

  1. concentrationthe mixture was concentrated
  2. customto provide a residue
  3. washThe solution was washed with 1.0 N aqueous sodium hydroxide
  4. dry with materialwas dried over sodium sulfate
  5. concentrationconcentrated
  6. customto provide a residue
  7. customThe residue was purified by flash column chromatography
  8. washeluting with 2% methanol/dichloromethane containing 0.2% aqueous ammonia

Sources & evidence

ORD record
ord-82d192c852514f7f85e2241731cc1019
Source dataset
uspto-grants-2007_06
Patent number
US07230022B2

Reaction notes

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