Acetonitrile → HCID 10270728, compound

HRID 2417378Notes

Reaction equation

Cl.N[C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[NH:8])=[CH:5][CH:4]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.[CH2:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22]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:57])C>>[Cl:12][C:13]1[CH:14]=[C:15]([CH:16]2[CH:22]3[CH2:23][C:24]4[C:29]([CH:21]3[C:3]3[C:4](=[CH:5][C:6]([C:7]([NH2:9])=[NH:8])=[CH:10][CH:11]=3)[NH:57]2)=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:18]=[CH:19][CH:20]=1

Participants

Reactant 5

HCID 6342Acetonitrile

HCID 7219Indene

HCID 114773-Chlorobenzaldehyde

HCID 122765Benzenecarboximidamide, 4-amino-, hydrochloride (1:1)

HCID 2734680Indium(III) trifluoromethanesulfonate

Product 1

HCID 10270728HCID 10270728, 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-chlorobenzaldehyde (14.0 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 24 hours. The desired product was purified using reverse phase HPLC. Mass spectrum: 374(M+1).

Workup

customThe desired product was purified

Sources & evidence

ORD record: ord-df6a1777c32a48b7af0e7c56048b3f18
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825208B2

Reaction notes

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