1,2-Dichloroethane → HCID 178438007, compound

HRID 734680Notes

Reaction equation

HRID 734680 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][C:13](=[O:15])[NH:12][C:11]([CH3:16])=[C:10]2[C:17]([OH:19])=O)=[CH:5][CH:4]=1.[NH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][N:27]=[C:26]2[CH2:32][CH3:33].C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[CH2:32]([C:26]1[C:25]2[C:29](=[CH:30][CH:31]=[C:23]([NH:22][C:17]([C:10]3[CH:9]([C:6]4[CH:7]=[CH:8][C:3]([C:2]([F:20])([F:21])[F:1])=[CH:4][CH:5]=4)[CH2:14][C:13](=[O:15])[NH:12][C:11]=3[CH3:16])=[O:19])[CH:24]=2)[NH:28][N:27]=1)[CH3:33]

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 178438005HCID 178438005, compound

Product 1

HCID 178438007HCID 178438007, compoundYield 17.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 5, Step 2 (125 mg, 0.418 mmol, 1.00 equiv), 5-amino-3-ethylindazole (67 mg, 0.418 mmol, 1.0 equiv), and EDC (96 mg, 0.501 mmol, 1.20 equiv) were suspended in 1.25 mL DMF. Et3N (0.070 mL, 0.501 mmol, 1.2 equiv) was added and the solution was stirred at room temperature for 18 hrs. 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 dried over Na2SO4, filtered, and concentrated en vacuo. The residue was triturated with EtOAc and CH2Cl2, filtered, and washed with CH2Cl2 to provide 32 mg (17%) of the title compound as an off white solid. MS (ES+) m/e 443 [M+H]+

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed twice with 1N HCl, once with satd
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated en vacuo
  6. customThe residue was triturated with EtOAc and CH2Cl2
  7. filtrationfiltered
  8. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-35c926c432b64d19970292359d25dc7d
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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