Ammonia → HCID 178481561, compound

HRID 2223067Notes

Reaction equation

HRID 2223067 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.[NH3:42]>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)=[NH:42])[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 222AmmoniaHCID 9830230HCID 9830230, compound

Product 1

HCID 178481561HCID 178481561, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

As illustrated in the scheme above, to 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) (0.029 g, 0.05 mmol) and silver triflate (0.038 g, 0.15 mmol) in dichloromethane (2 ml) was added a solution of ammonia (0.25 ml, 2M in methanol). The reaction mixture was stirred at room temperature for 3 h, diluted with dichloromethane (10 ml) and washed with brine (2×5 ml). The organic layer was dried with MgSO4 filtered, concentrated in vacuo. The residue was triturated with ether to give the title compound (0.008 g, 28%) as a pale yellow solid. 1H-NMR (CDCl3): δ 8.22 (d, J=9.2 Hz, 1H), 8.11 (d, J=8.4 Hz, 1H), 7.75 (br.s, 1H), 7.50-7.41 (m, 7H), 7.31 (d, J=8.8 Hz, 1H), 7.04 (m, 2H), 5.8 (br.s, 1H), 3.96 (t, J=9.2 Hz, 4H) 3.51 (s, 3H) and 3.05 (br.s, 4H).). (ESI) (M+H)+=587.

Workup

  1. washwashed with brine (2×5 ml)
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-c3012ee8aded488ca9240c8b38aff7ef
Source dataset
uspto-grants-2008_05
Patent number
US07375101B2

Reaction notes

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