1,2-Dichloroethane → HCID 178429199, compound

HRID 734717Notes

Reaction equation

HRID 734717 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([F:12])=[C:8]([NH2:11])[CH:9]=2)[NH:4][N:3]=1.[F:13][C:14]([F:33])([F:32])[C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:26][C:25](=[O:27])[NH:24][C:23]([CH3:28])=[C:22]2[C:29](O)=[O:30])=[CH:17][CH:16]=1.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([F:12])=[C:8]([NH:11][C:29]([C:22]3[CH:21]([C:18]4[CH:19]=[CH:20][C:15]([C:14]([F:33])([F:13])[F:32])=[CH:16][CH:17]=4)[CH2:26][C:25](=[O:27])[NH:24][C:23]=3[CH3:28])=[O:30])[CH:9]=2)[NH:4][N:3]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 160998632-Methyl-6-oxo-4-(4-(trifluoromethyl)phenyl)-1,4,5,6-tetrahydropyridine-3-carboxylic acidHCID 1785072033-chloro-6-fluoro-1H-indazol-5-amine

Product 1

HCID 178429199HCID 178429199, compoundYield 5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 39, Step 2 (125 mg, 0.668 mmol, 1.0 equiv) was combined with the product from Example 5, Step 2 (200 mg, 0.668 mmol, 1.0 equiv), EDC (153 mg, 0.802 mmol, 1.2 equiv) and Et3N (112 μL, 0.802 mmol, 1.2 equiv) in DMF (2 mL) and stirred at room temperature 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. The organic phase was concentrated en vacuo. The residue was purified by flash chromatography (20-100% EtOAc in Hexanes) and further purified by reverse-phase HPLC (10-75% CH3CN/H2O, 0.1% TFA over 20 minutes, retention time 13.9 min) to provide 15 mg (5%) of the title compound as a white solid. MS (ES+) m/e 467 [M+H]+

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed twice with 1N HCl, once with satd
  3. concentrationThe organic phase was concentrated en vacuo
  4. customThe residue was purified by flash chromatography (20-100% EtOAc in Hexanes)
  5. customfurther purified by reverse-phase HPLC (10-75% CH3CN/H2O, 0.1% TFA over 20 minutes, retention time 13.9 min)

Sources & evidence

ORD record
ord-231831db362b44c69582cfcd38de86ea
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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