1,2-Dichloroethane → 4-[4-Chloro-3-(methyloxy)phenyl]-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide

HRID 734754Notes

Reaction equation

[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[NH2:11].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:24][C:23](=[O:25])[NH:22][C:21]([CH3:26])=[C:20]2[C:27](O)=[O:28])=[CH:15][C:14]=1[O:30][CH3:31].C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:24][C:23](=[O:25])[NH:22][C:21]([CH3:26])=[C:20]2[C:27]([NH:11][C:3]2[CH:4]=[C:5]3[C:9](=[CH:10][C:2]=2[F:1])[NH:8][N:7]=[CH:6]3)=[O:28])=[CH:15][C:14]=1[O:30][CH3:31]

Participants

Conditions

Temperature: 30 °C

Procedure

6-Fluoro-1H-indazol-5-amine (102 mg, 0.676 mmol, 1.0 equiv) was combined with the product of Example 93, Step 4 (0.200 g, 0.676 mmol, 1.0 equiv), EDC (155 mg, 0.812 mmol, 1.2 equiv) and Et3N (113 μL, 0.812 mmol, 1.2 equiv) in DMF (2 mL) and stirred at 30° C. for 18 hours. The reaction mixture was 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. Solid precipitated out of the organic phase and was filtered and triturated with ether to provide 85.0 mg (29%) of the title compound as a white solid. MS (ES+) m/e 429 [M+H]+

Workup

customThe phases were separated
washthe organic phase was washed twice with 1N HCl, once with satd
customSolid precipitated out of the organic phase
filtrationwas filtered
customtriturated with ether

Sources & evidence

ORD record: ord-fde6ac4e9b4c4a2996f12cdabf9324cc
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592357B2

Reaction notes

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