2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 118025588, compound

HRID 1750551Notes

Reaction equation

COC1C=CC(C[O:10][CH:11]2[CH2:15][CH:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]([NH:24][C:25](=[O:37])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[N:32]3[N:36]=[CH:35][CH:34]=[N:33]3)[CH2:12]2)=CC=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(Cl)Cl.O>[OH:10][CH:11]1[CH2:15][CH:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]([NH:24][C:25](=[O:37])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[N:32]2[N:33]=[CH:34][CH:35]=[N:36]2)[CH2:12]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl N-{4-[(4-methoxyphenyl)methoxy]-2-[2-(2H-1,2,3-triazol-2-yl)benzamido]cyclopentyl}carbamate (1.85 g, 3.64 mmol) in DCM (36 ml) and water (0.364 ml) at 0° C. under an atmosphere of nitrogen was added 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile (CAS number 84-58-2; 1.655 g, 7.29 mmol). The reaction was stirred at 0° C. for 1 hour, then was partitioned between a saturated solution of sodium bicarbonate and DCM. The organics were filtered through a hydrophobic frit and concentrated in vacuo. The crude material was purified by column chromatography (silica, 0-100% ethyl acetate/petrol then 0-30% methanol/ethyl acetate) to afford the title compound.

Workup

customwas partitioned between a saturated solution of sodium bicarbonate and DCM
filtrationThe organics were filtered through a hydrophobic frit
concentrationconcentrated in vacuo
customThe crude material was purified by column chromatography (silica, 0-100% ethyl acetate/petrol

Sources & evidence

ORD record: ord-cbb5655f4baf4ce695b4aaed5598d0e0
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156829B2

Reaction notes

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