Chloroacetyl isocyanate → 2-[4-(2,4-dioxo-imidazolidin-1-yl)phenyl]-6-ethoxy-1-ethyl-1H-indole-3-carbonitrile

HRID 907156Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:22][CH3:23])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=3)=[CH:4][CH:3]=1.Cl[CH2:25][C:26]([N:28]=[C:29]=[O:30])=[O:27].C1CCN2C(=NCCC2)CC1>O1CCOCC1>[O:30]=[C:29]1[NH:28][C:26](=[O:27])[CH2:25][N:1]1[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH2:22][CH3:23])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=3)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2-(4-aminophenyl)-6-ethoxy-1-ethyl-1H-indole-3-carbonitrile (319 mg, 1.04 mmol) in 1,4-dioxane (3 mL) was treated with chloroacetyl isocyanate (0.10 mL, 1.17 mmol), and the resulting solution was warmed to 60° C. overnight. The solution was cooled, and DBU (0.20 mL, 1.31 mmol) was added. This mixture was stirred at ambient temperature overnight, and then was partitioned between water and ethyl acetate (50 mL each). The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate, filtered and evaporated. The residual material was triturated with ether, and the resulting solid was collected by filtration and dried under high vacuum to afford the title product (319 mg, 0.821 mmol, 79%).

Workup

temperatureThe solution was cooled
customwas partitioned between water and ethyl acetate (50 mL each)
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customevaporated
customThe residual material was triturated with ether
filtrationthe resulting solid was collected by filtration
customdried under high vacuum

Sources & evidence

ORD record: ord-7f554fa033af4a7fbb439deb6b4012ea
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013006B2

Reaction notes

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