5-Aminoisoquinoline → HCID 24885338, compound

HRID 2223059Notes

Reaction equation

HRID 2223059 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH:9]([N:14]=[C:15]=[S:16])[N:8]=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:6]=2[CH:23]=1.[CH:24]1[C:33]2[CH:32]=[CH:31][CH:30]=[C:29]([NH2:34])[C:28]=2[CH:27]=[CH:26][N:25]=1>ClCCl>[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:34][C:29]3[CH:30]=[CH:31][CH:32]=[C:33]4[C:28]=3[CH:27]=[CH:26][N:25]=[CH:24]4)=[S:16])[N:8]=[C:7]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:6]=2[CH:23]=1

Participants

4

Reactant 2

HCID 707665-AminoisoquinolineHCID 86600074HCID 86600074, compound2×

Product 1

HCID 24885338HCID 24885338, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As illustrated in the scheme above, to a solution of 7-chloro-1,3-dihydro-3-isothiocyanato-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one (INTERMEDIATE 7) (0.035 g, 0.1 mmol) in dichloromethane (5 ml) was added 5-isoquinolinamine (0.015 g, 0.1 mmol). The reaction mixture was heated at reflux for 17 hours. The solvent was evaporated in vacuo, the residue was triturated with ether and the title compound was obtained as a colorless solid (20 mg, 40%). 1H-NMR (CDCl3): δ 9.33 and 9.19 (2×s, 1H), 8.63 and 8.49 (2×d, J=5.6 Hz and J=6.0 Hz, 1H), 8.34 (br s, 1H), 8.02 (d, J=8.4 Hz, 1H), 7.92 (t, J=11.6 Hz, 2H), 7.58-7.32 (m, 10H), 6.03 (d, J=7.6 Hz, 1H) and 3.3 (s, 3H). MS (ESI) (M+H)+=486

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 17 hours
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-86f498e8730f494e8e44a26d81e8b844
Source dataset
uspto-grants-2008_05
Patent number
US07375101B2

Reaction notes

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