1,4-Dioxane → HCID 24804720, compound

HRID 1625003Notes

Reaction equation

I[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([C@@H:13]([CH3:17])[C:14]([NH2:16])=[O:15])[C:7]2=[O:12].[C:18]12([CH2:28][NH2:29])[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2.N12CCCN=C1CCCCC2.[O:41]1CCOC[CH2:42]1>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:18]12([CH2:28][NH:29][C:42]([C:2]3[C:3]4[CH:4]=[CH:5][N:6]([C@H:13]([C:14](=[O:15])[NH2:16])[CH3:17])[C:7](=[O:12])[C:8]=4[CH:9]=[CH:10][CH:11]=3)=[O:41])[CH2:25][CH:24]3[CH2:23][CH:22]([CH2:21][CH:20]([CH2:26]3)[CH2:19]1)[CH2:27]2

Participants

Conditions

Temperature: 110 °C

Procedure

A 5-mL process vial was charged with (S)-2-(5-iodo-1-oxoisoquinolin-2(1H)-yl)propanamide (90 mg, 0.0003 mol), 1-adamantanemethylamine (90 mg, 0.0005 mol), molybdenum hexacarbonyl (90 mg, 0.0004 mol), palladium acetate (8 mg, 0.00004 mol), 1,8-diazabicyclo[5.4.0]undec-7-ene (80 mg, 0.0005 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, 50-100% EtOAC/Hexane) 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, 50-100% EtOAC/Hexane)

Sources & evidence

ORD record: ord-67568e418d10414d8163f3b3013323e0
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779144B2

Reaction notes

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