Benzenemethanamine, 3,4-dichloro- → HCID 24805212, compound

HRID 1625010Notes

Reaction equation

[CH:1]1([N:4]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][C:10]=3I)[C:5]2=[O:15])[CH2:3][CH2:2]1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:20][NH2:21].N12CCCN=C1CCCCC2.[O:37]1CCOC[CH2:38]1>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:1]1([N:4]2[CH:13]=[CH:12][C:11]3[C:10]([C:38]([NH:21][CH2:20][C:19]4[CH:22]=[CH:23][C:24]([Cl:25])=[C:17]([Cl:16])[CH:18]=4)=[O:37])=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]2=[O:15])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 110 °C

Procedure

A 5-mL process vial was charged with 2-cyclopropyl-5-iodoisoquinolin-1(2H)-one (100 mg, 0.0004 mol), 3,4-dichloro-benzylamine (200 mg, 0.001 mol), molybdenum hexacarbonyl (90 mg, 0.0004 mol), palladium acetate (8 mg, 0.00004 mol), 1,8-diazabicyclo[5.4.0]undec-7-ene (200 mg, 0.001 mol) and 1,4-dioxane (2 mL, 0.02 mol). The vessel was sealed under air and exposed to microwave heating for 15 min at 110° C. The reaction tube was thereafter cooled to room temperature, and the mixture was concentrated and dissolved in a small volume of dichloromethane. The crude product was purified via flash column chromatography (12 g of silica gel, 50% EtOAC/Hexane) and then prep. HPLC to give the desired product as a white solid.

Workup

customThe vessel was sealed under air
temperatureThe reaction tube was thereafter cooled to room temperature
concentrationthe mixture was concentrated
dissolutiondissolved in a small volume of dichloromethane
customThe crude product was purified via flash column chromatography (12 g of silica gel, 50% EtOAC/Hexane)

Sources & evidence

ORD record: ord-ffc76557d1414adda89b36148284dad3
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779144B2

Reaction notes

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