2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → N-Ethyl-N'-[7-(3-pyridyl)[1,3]thiazolo[4',5': 3,4]benzo[d][1,3]thiazol-2-yl]urea

HRID 9152

Reaction equation

[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]3[N:16]=[C:17]([C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)[S:18][C:14]=3[CH2:13][CH2:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]3[N:16]=[C:17]([C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)[S:18][C:14]=3[CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 35 °C

Procedure

A suspension of N-ethyl-N′-[7-(3-pyridyl)-4,5-dihydro[1,3]thiazolo[4′,5′: 3,4]benzo[d]-[1,3]thiazol-2-yl]urea (10 mg, 0.028 mmol) and DDQ (13 mg, 0.056 mmol) in toluene (1 mL) was heated to about 35° C. for about 3 hrs. The reaction mixture was concentrated in vacuo and purified by preparative HPLC. 3 mg (30%) pure product was isolated. LC/MS 356 (MH+); RP-HPLC 14.25 min.

Workup

concentrationThe reaction mixture was concentrated in vacuo
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-990155086c5549828f0ac2fa7edc056a
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091227B2

Linked notes

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