1,4-Dioxane → HCID 24804886, compound

HRID 1625001Notes

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].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][NH2:26])=[CH:21][C:20]=1[C:27]([F:30])([F:29])[F:28].N12CCCN=C1CCCCC2.[O:42]1CCOC[CH2:43]1>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:16][C:14](=[O:15])[C@@H:13]([N:6]1[CH:5]=[CH:4][C:3]2[C:2]([C:43]([NH:26][CH2:25][C:22]3[CH:23]=[CH:24][C:19]([Cl:18])=[C:20]([C:27]([F:28])([F:29])[F:30])[CH:21]=3)=[O:42])=[CH:11][CH:10]=[CH:9][C:8]=2[C:7]1=[O:12])[CH3:17]

Participants

Conditions

Temperature: 110 °C

Procedure

A 5-mL process vial was charged with (S)-2-(5-iodo-1-oxoisoquinolin-2(1H)-yl)propanamide (100 mg, 0.0004 mol), (4-chloro-3-(trifluoromethyl)phenyl)methanamine (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, 50-100% EtOAC/Hexane) 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-7bf0be70dc2244e9bade659bc6ddd09f
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779144B2

Reaction notes

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