Diisopropylethylamine → HCID 22000409, compound

HRID 917501Notes

Reaction equation

HRID 917501 reaction equation
[NH2:1][C:2]([NH:4][CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][CH2:7]1)=[S:3].Br[CH:24]1[C:30](=O)[C:29]2[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=2[O:27][CH2:26][CH2:25]1.C(N(C(C)C)CC)(C)C>CCO>[CH2:15]([O:14][C:13](=[O:22])[NH:12][CH:9]1[CH2:10][CH2:11][CH:6]([CH2:5][NH:4][C:2]2[S:3][C:24]3[CH2:25][CH2:26][O:27][C:28]4[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=4[C:30]=3[N:1]=2)[CH2:7][CH2:8]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 138632344-Bromo-3,4-dihydro-2H-benzo[b]oxepin-5-oneHCID 22254014HCID 22254014, compound

Product 1

HCID 22000409HCID 22000409, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution containing benzyl N-(4-{[(aminocarbothioyl)amino]methyl}-cyclohexyl)-carbamate (3.45 g, 10.73 mmol), 4-bromo-2,3,4,5-tetrahydro-1-benzoxepin-5-one (2.60 g, 10.78 mmol), diisopropylethylamine (2.50 ml) and EtOH (50 ml) was heated at reflux for 4 hours. The solvent was removed and the residue was chromatographed on silica-gel eluting with 1:3 EtOAc/Hexane to yield 65% (3.2 g) of the product as a white solid: m.p. 124-127° C.; 1H-NMR (CDCl3) δ 1.09 (4H, pentet, J=10.4 Hz), 1.55 (1H, broad), 1.83 (2H, m), 2.04 (2H, broad), 3.10 (2H, t, J=6.2 Hz), 3.15 (2H, t, J=5.2 Hz), 3.43 (1H, broad) 4.33 (2H, t, J=5.2 Hz), 4.62 (1H, d, J=8.0 Hz), 5.08 (2H, s), 5.31 (1H, m), 7.00 (1H, dd, J=1.2 Hz, 7.8 Hz), 7.12 (2H, m), 7.35 (5H, s), 8.25 (1H, dd, J=1.7 Hz, 7.8 Hz); 464 (ESMS, MH+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customThe solvent was removed
  4. customthe residue was chromatographed on silica-gel
  5. washeluting with 1:3 EtOAc/Hexane

Sources & evidence

ORD record
ord-1a4896860b204d78bb3fe5266f9e89ad
Source dataset
uspto-grants-2007_09
Patent number
US07273880B2

Reaction notes

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