2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 11690152, compound

HRID 1787512Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]3[C:16]4[CH2:24][CH2:23][C:22]5[C:18](=[CH:19][N:20]([CH2:25][CH2:26][OH:27])[N:21]=5)[C:17]=4[S:28][C:14]=3[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:11]=[CH:12][N:13]=[C:14]3[C:15]=2[C:16]2[CH:24]=[CH:23][C:22]4[C:18](=[CH:19][N:20]([CH2:25][CH2:26][OH:27])[N:21]=4)[C:17]=2[S:28]3)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirring solution of 2-{6-[(3-chloro-4-fluorophenyl)amino]-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-2-yl}ethanol (2.6 g, 6.25 mmol) in dioxane (25 mL) was added 2,3-dichloro-5,6-dicyanobenzoquinone (2.1 g, 9.38 mmol). The reaction mixture was heated to 90° C. for 2.5 h. The solid was filtered and separated by column chromatograph (90% methylene chloride/10% methanol) to give 2-[6-(3-chloro-4-fluoro-phenylamino)-10-thia-2,3,7,9-tetraazacyclopenta[a]fluoren-2-yl]-ethanol as a brown solid (3.0 g, yield 116% containing some carried over silica gel). 1H-NMR (DMSO-d6) δ 9.25 (bs, 1H), 8.80 (s, 1H), 8.60 (s, 1H), 8.40 (t, 1H), 7.90 (d, 1H), 7.80 (d, 1H), 7.60 (m, 1H), 7.40 (t, 1H), 4.50 (t, 2H), 3.90 (t, 2H); LCMS RT=2.95 min; [M+H]+=414.2.

Workup

filtrationThe solid was filtered
customseparated by column chromatograph (90% methylene chloride/10% methanol)

Sources & evidence

ORD record: ord-0525bedf2ab44b1086154f575b1dbaf9
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511048B2

Reaction notes

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