1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178446171, compound

HRID 2374402Notes

Reaction equation

C(O[C:4]([C:6]1[C:11](=[O:12])[N:10]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[N:9]2[CH:18]=[C:19]([F:21])[CH:20]=[C:8]2[C:7]=1[OH:22])=O)C.[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([I:30])=[CH:26][C:25]=1[S:31]([NH2:34])(=[O:33])=[O:32].N12CCCN=C1CCCCC2>N1C=CC=CC=1>[F:21][C:19]1[CH:20]=[C:8]2[C:7]([OH:22])=[C:6]([C:4]3[NH:23][C:24]4[CH:29]=[CH:28][C:27]([I:30])=[CH:26][C:25]=4[S:31](=[O:33])(=[O:32])[N:34]=3)[C:11](=[O:12])[N:10]([CH2:13][CH2:14][CH:15]([CH3:16])[CH3:17])[N:9]2[CH:18]=1

Participants

Conditions

Temperature: 120 °C

Procedure

6-Fluoro-4-hydroxy-1-(3-methyl-butyl)-2-oxo-1,2-dihydro-pyrrolo[1,2-b]pyridazine-3-carboxylic acid ethyl ester (Example 141, 136.7 mg, 0.441 mmol) and 2-amino-5-iodo-benzenesulfonamide (Example 4a, 131.3 mg, 0.441 mmol) were mixed in anhydrous pyridine (2 mL) and heated at 120° C. for 3 h. 1,8-Diazabicyclo[5.4.0]undec-7-ene (200 μL) was added and the mixture was heated at 120° C. for 16 h. Purification by flash column chromatography (Merck silica gel 60, 40-63 μm, 20% ethyl acetate in hexanes) afforded the desired product, 6-fluoro-4-hydroxy-3-(7-iodo-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-1-(3-methyl-butyl)-pyrrolo[1,2-b]pyridazin-2-one (0.047 g, 0.086 mmol, 19.5% yield) as a dark purple solid. LC-MS (ESI) calcd for C19H18FIN4O4S 544.01. found 544.97 [M+H+].

Workup

temperaturethe mixture was heated at 120° C. for 16 h
customPurification by flash column chromatography (Merck silica gel 60, 40-63 μm, 20% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-962ee995c04a462dbe1b7847d4abe2d6
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07462611B2

Reaction notes

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