Indene → HCID 10293466, compound

HRID 2417379Notes

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.C([O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][C:17]=1[O:24][CH3:25])(=O)C.[CH2:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27]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.[OH-].[NH4+]>C(#N)C>[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]2[CH:27]3[CH2:28][C:29]4[C:34]([CH:26]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:33][CH:32]=[CH:31][CH:30]=4)=[CH:18][C:17]=1[O:24][CH3:25]

Participants

Conditions

Temperature: 70 °C

Procedure

4-amino-benzamidine mono HCl salt (17.2 mg, 0.1 mmole) was suspended in acetonitrile (1 mL). The suspension was treated with 4-acetoxy-3-methoxybenzaldehyde (19.0 mg, 0.1 mmole) and indene(11.6 mg, 0.1 mmole). Indium triflate (11.2 mg, 0.02 mmole) was added and the reaction was heated at 70° C. for 48 hours. To the above mixture was added 100 uL of ammonium hydroxide. After stirring at rt overnight, the desired product 6-(4-Hydroxy-3-methoxy-phenyl)-5,6a,7,11b-tetrahydro-6H-indeno[2,1-c]quinoline-2-carboxamidine was purified using reverse phase HPLC. Mass spectrum: 385(M+1).

Workup

customthe desired product 6-(4-Hydroxy-3-methoxy-phenyl)-5,6a,7,11b-tetrahydro-6H-indeno[2,1-c]quinoline-2-carboxamidine was purified

Sources & evidence

ORD record: ord-871d08bad1f948efb91b4e3c1b43e6c9
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825208B2

Reaction notes

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