Triethylamine → 5-(2-chlorophenyl)-1,2,3,6,7,9-hexahydro-3-hydroxy-N-(4-methoxy-2-nitrophenyl)-2-oxo-1-(2-phenylethyl)-8H-pyrido[4',3':4,5]thieno[2,3-e]-1,4-diazepine-8-carbothioamide

HRID 1836204Notes

Reaction equation

HRID 1836204 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[C:27]3[CH2:28][CH2:29][NH:30][CH2:31][C:26]=3[S:25][C:10]=2[N:11]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:12](=[O:16])[CH:13]([OH:15])[N:14]=1.C(N(CC)CC)C.[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([N:47]=[C:48]=[S:49])=[C:43]([N+:50]([O-:52])=[O:51])[CH:42]=1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[C:27]3[CH2:28][CH2:29][N:30]([C:48](=[S:49])[NH:47][C:44]4[CH:45]=[CH:46][C:41]([O:40][CH3:39])=[CH:42][C:43]=4[N+:50]([O-:52])=[O:51])[CH2:31][C:26]=3[S:25][C:10]=2[N:11]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:12](=[O:16])[CH:13]([OH:15])[N:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1410064-Methoxy-2-nitrophenyl isothiocyanateHCID 158879725-(2-chlorophenyl)-1,2,3,6,7,9-hexahydro-3-hydroxy-1-(2-phenylethyl)-8H-pyrido[4',3':4,5]thieno[2,3-e]-1,4-diazepine-2-one

Product 1

HCID 158879735-(2-chlorophenyl)-1,2,3,6,7,9-hexahydro-3-hydroxy-N-(4-methoxy-2-nitrophenyl)-2-oxo-1-(2-phenylethyl)-8H-pyrido[4',3':4,5]thieno[2,3-e]-1,4-diazepine-8-carbothioamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(2-chlorophenyl)-1,2,3,6,7,9-hexahydro-3-hydroxy-1-(2-phenylethyl)-8H-pyrido[4′,3′:4,5]thieno[2,3-e]-1,4-diazepine-2-one (0.167 g, 0.29 mmol) is dissolved in dichloromethane (2 ml). Triethylamine (0.06 ml, 0.44 mmol) then 4-methoxy 2-nitrophenylisothiocyanate (0.062 g, 0.29 mmol) are added. After agitation at 23° C. for 2 hours, the solvent is evaporated off. After purification by chromatography on a silica column (eluent: dichloromehane-methanol: 98-2), the fractions contining only the product are evaporated. The solid is taken up in ether and a drop of dichloromethame and a drop of acetone are added. After filtration on flit and washing the solid with ether, the desired product is obtained in the form of a yellow powder (0.08 g, 41%).

Workup

  1. customthe solvent is evaporated off
  2. customAfter purification by chromatography on a silica column (eluent: dichloromehane-methanol: 98-2)
  3. customare evaporated
  4. additiona drop of dichloromethame and a drop of acetone are added
  5. filtrationAfter filtration on flit
  6. washwashing the solid with ether

Sources & evidence

ORD record
ord-4124d29d39784078bf0974d3ba775bc4
Source dataset
uspto-grants-2004_08
Patent number
US06777408B1

Reaction notes

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