Indene → HCID 69892862, compound

HRID 2417389Notes

Reaction equation

HRID 2417389 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.[CH3:12][O:13][C:14](=[O:40])[C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:25]([O:36][CH3:37])=[CH:24][C:23]=2[CH:38]=O)=[CH:17][CH:16]=1.[CH2:41]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42]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>[CH3:12][O:13][C:14](=[O:40])[C:15]1[CH:16]=[CH:17][C:18]([O:21][C:22]2[CH:27]=[C:26]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:25]([O:36][CH3:37])=[CH:24][C:23]=2[CH:38]2[CH:42]3[CH2:43][C:44]4[C:49]([CH:41]3[C:11]3[C:3](=[CH:4][CH:5]=[C:6]([C:7](=[NH:9])[NH2:8])[CH:10]=3)[NH:2]2)=[CH:48][CH:47]=[CH:46][CH:45]=4)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 7219IndeneHCID 122765Benzenecarboximidamide, 4-amino-, hydrochloride (1:1)HCID 2734680Indium(III) trifluoromethanesulfonateHCID 88006991HCID 88006991, compound

Product 1

HCID 69892862HCID 69892862, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

4-amino-benzamidine mono HCl salt (120 mg, 0.7 mmole) was suspended in acetonitrile (4 mL). The suspension was treated with 4-(5-Benzyloxy-2-formyl-4-methoxy-phenoxy)-benzoic acid methyl ester (274 mg, 0.7 mmole) and indene (162 mg, 1.4 mmole). Indium triflate (79 mg, 0.14 mmole) was added and the reaction was heated at 75° C. for 18 hours to give 4-[5-Benzyloxy-2-(2-carbamimidoyl-5,6a,7,11b-tetrahydro-6H-indeno[2,1-c]quinolin-6-yl)-4-methoxy-phenoxy]-benzoic acid methyl ester which was purified by column chromatography (10%methanol in ethyl acetate).

Sources & evidence

ORD record
ord-7acb104fe1a7478198d7d2f668da3ad5
Source dataset
uspto-grants-2004_11
Patent number
US06825208B2

Reaction notes

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