1,2-Dichloroethane → HCID 11360518, compound

HRID 734662Notes

Reaction equation

HRID 734662 reaction equation
[F: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>[F: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

9

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 880121H-Indazol-5-amineHCID 160998624-(4-Fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylic acid

Product 1

HCID 11360518HCID 11360518, compoundYield 13.3%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

The product of step 2 (128 mg, 0.514 mmol, 1.00 equiv), 1H-indazol-5-amine (82.0 mg, 0.617 mmol, 1.20 equiv), EDC (118 mg, 0.617 mmol, 1.20 equiv), and DMAP (10 mg, catalytic) were suspended in 2.0 mL DMF. Et3N (0.086 mL, 1.35 mmol, 2.4 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 25.0 mg (13%) of the title compound as a white solid. MS (ES+) m/e 365 [M+H]+

Workup

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

Sources & evidence

ORD record
ord-4b53950c12c1493583899061eaf6412d
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

Loading…