2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → N-Ethyl-N'-(8H-[1,3]thiazolo[4,5-g]indol-2-yl)urea

HRID 9157

Reaction equation

[S:1]1[C:12]2[C:11]3[NH:10][CH:9]=[CH:8][C:7]=3[CH2:6][CH2:5][C:4]=2[N:3]=[C:2]1[NH:13][C:14]([NH:16][CH2:17][CH3:18])=[O:15].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[CH2:17]([NH:16][C:14]([NH:13][C:2]1[S:1][C:12]2[C:11]3[NH:10][CH:9]=[CH:8][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1)=[O:15])[CH3:18]

Participants

Conditions

Temperature: 45 °C

Procedure

To a suspension of N-(5,8-dihydro-4H-[1,3]thiazolo[4,5-g]indol-2-yl)-N′-ethylurea (81 mg, 0.308 mmol) in toluene (3.5 mL) was added DDQ (78 mg, 0.34 mmol). The reaction mixture was stirred at about 45° C. for about 4 hrs. The reaction mixture was pumped down and the crude material was purified by preparative HPLC. 3 mg (4%, 2 steps) pure product was isolated. LC/MS 262 (MH+); RP-BPLC RT 10.45 min.

Workup

customthe crude material was purified by preparative HPLC
custom3 mg (4%, 2 steps) pure product was isolated
customRP-BPLC RT 10.45 min.

Sources & evidence

ORD record: ord-5a0dc76b8b9c408797b9d2afd2580814
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091227B2

Linked notes

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