Pyridine → 6-(3-(4-Acetylpiperazin-1-yl)propoxy)-3-(3,5-difluorophenyl)-2-(pyridin-3-yl)-1H-inden-1-one

HRID 331317Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH2:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)=[CH:15][CH:16]=3)[C:11](=[O:28])[C:10]=2[C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.N1C=CC=CC=1.[C:41](OC(=O)C)(=[O:43])[CH3:42]>C(Cl)Cl>[C:41]([N:25]1[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][CH2:19][O:18][C:14]2[CH:13]=[C:12]3[C:17]([C:9]([C:4]4[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=4)=[C:10]([C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)[C:11]3=[O:28])=[CH:16][CH:15]=2)[CH2:23][CH2:24]1)(=[O:43])[CH3:42]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 10 mL round-bottomed flask, 6-(3-(piperazin-1-yl)propoxy)-3-(3,5-difluorophenyl)-2-(pyridin-3-yl)-1H-inden-1-one (40 mg, 0.09 mmol) obtained in Step 1 of Example 66 and CH2Cl2 (2 mL, 0.05M) were charged. Pyridine (0.01 mL, 1.2 eq) was added and then the mixture was cooled to 0° C. and treated with acetic anhydride (0.01 mL, 1.2 eq). After being stirred for 15 h, the mixture was diluted with CH2Cl2 and washed with H2O and brine. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by being purified by silica gel column chromatography (CH2Cl2/MeOH=9:1) and being purified by prep. HPLC (20% H2O/CH3CN) to provide the title compound (25.9 mg, 59%).

Workup

washwashed with H2O and brine
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified
customby being purified by silica gel column chromatography (CH2Cl2/MeOH=9:1)
custombeing purified by prep

Sources & evidence

ORD record: ord-67cf615f91b24d64b1aa081d788e09e9
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877747B2

Reaction notes

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