Potassium Carbonate → HCID 68864518, compound

HRID 494148Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:17]2[C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=3)[N:14]=[C:13](Br)[C:12]=2[N:11]2[CH2:29][CH2:30][N:31]([CH3:34])[C:32](=[O:33])[C:10]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=1>CN1CCCC1=O.[Cu]I>[CH2:1]([O:8][C:9]1[C:17]2[C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=3)[N:14]=[C:13]([N:43]3[CH:44]=[CH:45][CH:46]=[CH:47][C:42]3=[O:41])[C:12]=2[N:11]2[CH2:29][CH2:30][N:31]([CH3:34])[C:32](=[O:33])[C:10]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 10-(benzyloxy)-2-(3-chloro-4-fluorobenzyl)-8-methyl-4-bromo-7,8-dihydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (0.15 g, 0.28 mmol), copper (I) iodide (27 mg, 0.14 mmol), potassium carbonate (76 mg, 0.55 mmol), and 2-hydroxypyridine (52 mg, 0.55 mmol) in N-methyl-2-pyrrolidinone (2.7 mL) was stirred in an oil bath at 140° C. for 3 hours. The resultant mixture was filtered and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a 1-5% methanol in chloroform gradient. Collection and concentration of appropriate fractions provided the title compound. ES MS M+1=560

Workup

filtrationThe resultant mixture was filtered
concentrationconcentrated under vacuum
customCollection and concentration of appropriate fractions

Sources & evidence

ORD record: ord-b319fcd529ad48309b9ea44a0811c1d4
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538112B2

Reaction notes

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