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1,2-Dichloroethane → HCID 11429770, compound

HRID 734701
Notes
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Reaction equation

HRID 734701 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:21])[CH2:5][CH:6]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[C:7]=1[C:8]([OH:10])=O.[NH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[C:30]([CH3:32])[CH:31]=1)[NH:28][N:27]=[CH:26]2.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[CH3:1][C:2]1[NH:3][C:4](=[O:21])[CH2:5][CH:6]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[C:7]=1[C:8]([NH:22][C:23]1[CH:24]=[C:25]2[C:29](=[C:30]([CH3:32])[CH:31]=1)[NH:28][N:27]=[CH:26]2)=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 13820227-methyl-1H-indazol-5-amineHCID 160998652-Methyl-4-(2-naphthalenyl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid

Product 1

HCID 11429770HCID 11429770, compoundYield 13.3%

Reagents, catalysts & solvents 3

HCID 313
Hydrochloric Acid
Solvent
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 1, Step 2 (180 mg, 0.64 mmol, 1.00 equiv), 5-amino-7-methylindazole (94 mg, 0.64 mmol, 1.0 equiv), and EDC (147 mg, 0.768 mmol, 1.20 equiv) were suspended in 1.5 mL DMF. Et3N (0.107 mL, 0.768 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 35 mg (13%) of the title compound as an off white solid. MS (ES+) m/e 434 [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-8f9a0149e77241759cfddab221044160
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07592357B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes