Tetrahydrofuran → HCID 57671888, compound

HRID 871999Notes

Reaction equation

HRID 871999 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:33])=[C:6]([CH:32]=1)[O:7][CH2:8][C:9]1[C:10]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:24]=2[O:30][CH3:31])=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]([CH3:19])[C:16](=[O:20])[C:15]([CH3:22])([CH3:21])[NH:14]2.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.[O:40]1CCC[CH2:41]1>CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:33])=[C:6]([CH:32]=1)[O:7][CH2:8][C:9]1[C:10]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:41]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[O:40])=[CH:25][C:24]=2[O:30][CH3:31])=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]([CH3:19])[C:16](=[O:20])[C:15]([CH3:22])([CH3:21])[NH:14]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 8083MorpholineHCID 252112638-(5-Fluoro-2-methylphenoxymethyl)-7-(4-hydroxy-2-methoxyphenyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

Product 1

HCID 57671888HCID 57671888, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A mixture of 8-(5-fluoro-2-methylphenoxymethyl)-7-(4-hydroxy-2-methoxyphenyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Compound No. 11, 153 mg, 0.340 mmol), 1,1′-carbonyldiimiazole (95.6 mg, 0.590 mmol), and 4-dimethylaminopyridine (5.2 mg, 0.043 mmol) was dissolved in anhydrous tetrahydrofuran (3 mL) and stirred for 1 hour at room temperature. After morpholine (58.3 μL, 0.666 mmol) was added to the reaction mixture and the mixture was stirred for 2 hour, the mixture was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (61.2 mg) as a colorless solid. (Yield 32%)

Workup

  1. stirringthe mixture was stirred for 2 hour
  2. customthe mixture was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-255b0beef46740f7a6c1199999629289
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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