Indene → 6-(5-Hydroxy-4'-isopropyl-4-methoxy-biphenyl-2-yl)-5,6a,7,11b-tetrahydro-6h-indeno[2,1-c]quinoline-2-carboxamidine

HRID 2417383Notes

Reaction equation

HRID 2417383 reaction equation
Cl.[NH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[NH:8])=[CH:5][CH:4]=1.[OH:12][C:13]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=2)[C:16]([CH:28]=O)=[CH:15][C:14]=1[O:30][CH3:31].[CH2:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33]1.[O-]S(C(F)(F)F)(=O)=O.[In+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>C(#N)C>[OH:12][C:13]1[C:14]([O:30][CH3:31])=[CH:15][C:16]([CH:28]2[CH:33]3[CH2:34][C:35]4[C:40]([CH:32]3[C:11]3[C:3](=[CH:4][CH:5]=[C:6]([C:7]([NH2:9])=[NH:8])[CH:10]=3)[NH:2]2)=[CH:39][CH:38]=[CH:37][CH:36]=4)=[C:17]([C:19]2[CH:20]=[CH:21][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:23][CH:24]=2)[CH:18]=1

Participants

6

Reactant 4

HCID 7219IndeneHCID 122765Benzenecarboximidamide, 4-amino-, hydrochloride (1:1)HCID 2734680Indium(III) trifluoromethanesulfonateHCID 22633322HCID 22633322, compound

Product 1

HCID 226332196-(5-Hydroxy-4'-isopropyl-4-methoxy-biphenyl-2-yl)-5,6a,7,11b-tetrahydro-6h-indeno[2,1-c]quinoline-2-carboxamidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

4-amino-benzamidine mono HCl salt (34.5 mg, 0.2 mmole) was suspended in acetonitrile (1 mL). The suspension was treated with 5-Hydroxy-4′-isopropyl-4-methoxy-biphenyl-2-carbaldehyde (27.0 mg, 0.1 mmole) and indene(23.2 mg, 0.2 mmole). Indium triflate (11.2 mg, 0.02 mmole) was added and the reaction was heated at 70° C. for 24 hours. The desired product was purified using reverse phase HPLC. Mass spectrum: 504 (M+1).

Workup

  1. customThe desired product was purified

Sources & evidence

ORD record
ord-822ec93ebb484fc1b13aca28310742bc
Source dataset
uspto-grants-2004_11
Patent number
US06825208B2

Reaction notes

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