Dimethylformamide → HCID 22291904, compound

HRID 457331Notes

Reaction equation

HRID 457331 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:15]4[CH:17]=[C:18]([NH:21][C:22](=[O:30])[C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=5[Cl:29])[CH:19]=[CH:20][C:14]=4[CH2:13][CH2:12][C:11]=3[C:10]([C:31]([NH2:33])=[O:32])=[N:9]2)=[CH:4][CH:3]=1.[CH3:34][N:35](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:22]([NH:21][C:18]1[CH:19]=[CH:20][C:14]2[CH2:13][CH2:12][C:11]3[C:10]([C:31]([NH2:33])=[O:32])=[N:9][N:8]([C:5]4[CH:6]=[CH:7][C:2]([C:34]#[N:35])=[CH:3][CH:4]=4)[C:16]=3[C:15]=2[CH:17]=1)=[O:30]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 22291757HCID 22291757, compound

Product 1

HCID 22291904HCID 22291904, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

1-(4-Bromophenyl)-8-[(2-chlorobenzoyl)amino]-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide (5.2 g) and Zn(CN)2 (0.9 g) were dissolved in 100 ml DMF under N2. Then Pd(Ph3P)4 (1.38 g) was added. The reaction mixture was heated up to 100° C. under N2 for 12 hours. After the reaction is completed by HPLC, the solvent was evaporated, and the residue was suspended in ethyl acetate and water. After filtration, and washing with water and ethyl acetate, the filtrate of the organic layer was separated and dried with Na2SO4. After filtration and evaporation of solvent, the residue was triturated with ether. Solid obtained was filtered and washed with ether, then dried under vacuum. The desired compound (3.4 g) was obtained and characterized by 1H NMR, LC-MS (468, M+1), and CHN analysis. IKK-2 resin IC50≦1 μM.

Workup

  1. customthe solvent was evaporated
  2. filtrationAfter filtration
  3. washwashing with water and ethyl acetate
  4. customthe filtrate of the organic layer was separated
  5. dry with materialdried with Na2SO4
  6. filtrationAfter filtration and evaporation of solvent
  7. customthe residue was triturated with ether
  8. customSolid obtained
  9. filtrationwas filtered
  10. washwashed with ether
  11. customdried under vacuum

Sources & evidence

ORD record
ord-ad200efb86034baa896cbcbee0588b75
Source dataset
uspto-grants-2007_03
Patent number
US07186743B2

Reaction notes

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