Acetonitrile → HCID 10225554, compound

HRID 2417380Notes

Reaction equation

HRID 2417380 reaction equation
Cl.N[C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[NH:8])=[CH:5][CH:4]=1.[O:12]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH2:28]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:64])C>>[O:12]([C:19]1[CH:20]=[C:21]([CH:22]2[CH:33]3[CH:32]([C:31]4[CH:30]=[CH:29][CH:28]=[CH:27][C:36]=4[CH2:35][CH2:34]3)[C:3]3[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[NH:8])=[CH:5][C:4]=3[NH:64]2)[CH:24]=[CH:25][CH:26]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 99381,2-DihydronaphthaleneHCID 382843-PhenoxybenzaldehydeHCID 122765Benzenecarboximidamide, 4-amino-, hydrochloride (1:1)HCID 2734680Indium(III) trifluoromethanesulfonate

Product 1

HCID 10225554HCID 10225554, compound

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 3-phenoxybenzaldehyde (19.8 mg, 0.1 mmole) and 1,2-dihydronapthalene(13.0 mg, 0.1 mmole). Indium triflate (11 mg, 0.02 mmole) was added and the reaction was heated at 70° C. for 48 hours. The desired products were purified using reverse phase HPLC. Mass spectrum: 446 (M+1).

Workup

  1. customThe desired products were purified

Sources & evidence

ORD record
ord-5900143dfdb3467a85055df15d696c4d
Source dataset
uspto-grants-2004_11
Patent number
US06825208B2

Reaction notes

Loading…