1,2-Dichloroethane → HCID 178487581, compound

HRID 734752Notes

Reaction equation

HRID 734752 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[NH:4][N:3]=1.[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:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][N:3]=[C:2]3[CH3:1])=[O:28])=[CH:15][C:14]=1[O:30][CH3:31]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 688272564-[4-Chloro-3-(methyloxy)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acidHCID 178434299HCID 178434299, compound

Product 1

HCID 178487581HCID 178487581, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

3-Methyl-1H-indazol-5-amine (87 mg, 0.592 mmol, 1.0 equiv) was combined with the product of Example 93, Step 4 (175 mg, 0.592 mmol, 1.0 equiv), EDC (134 mg, 0.710 mmol, 1.2 equiv) and Et3N (99 μL, 0.710 mmol, 1.2 equiv) in DMF (1.75 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 155 mg (62%) of the title compound as a white solid. MS (ES+) m/e 425 [M+H]+

Workup

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

Sources & evidence

ORD record
ord-27f59b013ecc4c5bada7fa8387897ed6
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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