Water → (3E)-3-[4-{6-[(2,3-dihydroxypropyl)(methyl)amino]pyridin-3-yl}-5,5-dimethylfuran-2(5H)-ylidene]-5,6-difluoro-1,3-dihydro-2H-indol-2-one

HRID 537938Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6](=[O:12])/[C:5]/2=[C:13]1/[O:14][C:15]([CH3:26])([CH3:25])[C:16]([C:18]2[CH:19]=[N:20][C:21](F)=[CH:22][CH:23]=2)=[CH:17]/1.[CH3:27][NH:28][CH2:29][CH:30]([OH:33])[CH2:31][OH:32].O>CN(C=O)C>[OH:33][CH:30]([CH2:31][OH:32])[CH2:29][N:28]([CH3:27])[C:21]1[N:20]=[CH:19][C:18]([C:16]2[C:15]([CH3:26])([CH3:25])[O:14]/[C:13](=[C:5]3/[C:6](=[O:12])[NH:7][C:8]4[C:4]/3=[CH:3][C:2]([F:1])=[C:10]([F:11])[CH:9]=4)/[CH:17]=2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (3E)-5,6-difluoro-3-[4-(6-fluoropyridin-3-yl)-5,5-dimethylfuran-2(5H)-ylidene]-1,3-dihydro-2H-indol-2-one (50 mg, 0.14 mmol) and 3-methylamino-1,2-propanediol (50 mg, 0.48 mmol) in 5 mL of DMF was heated in 100° C. bath under nitrogen for 16 hours. The mixture was cooled to room temp and poured into 100 mL of water. The precipitates were filtered, washed with water and dried in vacuo to give (3E)-3-[4-{6-[(2,3-dihydroxypropyl)(methyl)amino]pyridin-3-yl}-5,5-dimethylfuran-2(5H)-ylidene]-5,6-difluoro-1,3-dihydro-2H-indol-2-one as a brown solid. Yield: 51 mg, 82%.

Workup

temperatureThe mixture was cooled to room temp
filtrationThe precipitates were filtered
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-fd15b9997bce41c780da6270f66c3a68
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865682B2

Reaction notes

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