1,2-Dichloroethane → 4-(4-Chlorophenyl)-N-1H-indazol-5-yl-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide

HRID 734668Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([OH:18])=O)=[CH:4][CH:3]=1.[NH:19]1[C:27]2[C:22](=[CH:23][C:24]([NH2:28])=[CH:25][CH:26]=2)[CH:21]=[N:20]1.C(Cl)CCl.CCN(CC)CC>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOC(C)=O.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([NH:28][C:24]2[CH:23]=[C:22]3[C:27](=[CH:26][CH:25]=2)[NH:19][N:20]=[CH:21]3)=[O:18])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The product of step 2 (494 mg, 1.86 mmol, 1.00 equiv), 1H-indazol-5-amine (296 mg, 2.23 mmol, 1.20 equiv), EDC (426 mg, 2.23 mmol, 1.20 equiv), and DMAP (10 mg, catalytic) were suspended in 8.0 mL DMF. Et3N (0.621 mL, 4.46 mmol, 1.00 equiv) was added and the solution was heated to 80° C. for 2 hours. The reaction mixture was cooled to room temperature and diluted with EtOAc and 1N HCl. The phases were separated, and the organic phase was washed twice with 1N HCl, once with satd. NaHCO3, and once with satd. NaCl. The organic phase was dried over Na2SO4, filtered, and concentrated en vacuo. The residue was purified by flash chromatography (100% EtOAc) to provide 0.120 g (17%) of the title compound as a white solid. MS (ES+) m/e 399 [M+H]+

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe phases were separated
washthe organic phase was washed twice with 1N HCl, once with satd
dry with materialThe organic phase was dried over Na2SO4
filtrationfiltered
concentrationconcentrated en vacuo
customThe residue was purified by flash chromatography (100% EtOAc)

Sources & evidence

ORD record: ord-6b05044855b54cebbf1af22af36cf768
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592357B2

Reaction notes

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