HCID 9830230, compound → HCID 178481558, compound

HRID 2223066Notes

Reaction equation

HRID 2223066 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH:9]([NH:14][C:15]([NH:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:21]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:20][CH:19]=3)=S)[N:8]=[C:7]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[Cl:40])[C:6]=2[CH:41]=1.[Na+].[Na+].[N:44]#[C:45][NH-:46].N#C[NH-]>ClCCl.[O-]S(C(F)(F)F)(=O)=O.[Ag+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH:9]([NH:14][C:15]([NH:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:21]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:20][CH:19]=3)=[N:46][C:45]#[N:44])[N:8]=[C:7]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[Cl:40])[C:6]=2[CH:41]=1

Participants

5

Reactant 2

HCID 9830230HCID 9830230, compoundHCID 129750152HCID 129750152, compound

Product 1

HCID 178481558HCID 178481558, compoundYield 380%

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

As illustrated in the scheme above, a solution of N-[7-chloro-5-(2-chlorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-N′-[4-(4-morpholinyl)-1-naphthalenyl]-thiourea (EXAMPLE 11, made according to General Procedure 3) (0.058 g, 0.1 mmol) and silver triflate (0.077 g, 0.3 mmol) in dichloromethane (2 ml) was combined with cyanamide disodium salt (1 mmol) and stirred at room temperature for 3 h. The reaction mixture was then diluted with dichloromethane (10 ml) and washed with brine (2×5 ml). The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The residue was washed with ether (2×10 ml) and the polar isomer of the title compound (0.023 g, 380%) was obtained as pale yellow solid. The ether layer was concentrated in vacuo and purified by column chromatography (1:1 EtOAc:CH2Cl2) to give the non-polar isomer of the title compound (0.009 g, 15%) as a colorless solid.

Workup

  1. washwashed with brine (2×5 ml)
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe residue was washed with ether (2×10 ml)

Sources & evidence

ORD record
ord-85982188bc1849d2acdf52b5a6c4319c
Source dataset
uspto-grants-2008_05
Patent number
US07375101B2

Reaction notes

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