4-Chloroaniline → HCID 10292824, compound

HRID 2109600Notes

Reaction equation

HRID 2109600 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]3[C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=[CH:14][N:13]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(Cl)CCl>[Cl:21][C:22]1[CH:28]=[CH:27][C:25]([NH:26][C:18]([C:17]2[C:12]([NH:11][C:7]3[CH:6]=[C:5]4[C:10](=[CH:9][CH:8]=3)[N:1]=[CH:2][CH:3]=[CH:4]4)=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:20])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 78124-ChloroanilineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 21959464HCID 21959464, compound

Product 1

HCID 10292824HCID 10292824, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 2-(6-quinolylamino)pyridine-3-carboxylic acid (250 mg, from Step A). and 4-chloroaniline (120 mg) and DIEA (220 ul) in DMF (15 ml) was added EDC (220 mg) and HOBt (130 mg). The reaction was stirred at 50° C. for 3 h. The solution was evaporated under reduced pressure and mixed with CH2Cl2 (50 ml). The resulting solution was washed with 1N HCl, saturated NaHCO3, H2O and brine. The organic layer was dried over Na2SO4, evaporated under reduced pressure and triturated with CH2Cl2. The precipitate was filtered and washed with EtOH to give the titled compound. MS (ES+): 375 (M+H)+; (ES−): 373 (M−H)−. Calc'd for C21H15ClN4O−374.8.

Workup

  1. customThe solution was evaporated under reduced pressure
  2. additionmixed with CH2Cl2 (50 ml)
  3. washThe resulting solution was washed with 1N HCl, saturated NaHCO3, H2O and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated under reduced pressure
  6. customtriturated with CH2Cl2
  7. filtrationThe precipitate was filtered
  8. washwashed with EtOH

Sources & evidence

ORD record
ord-7413f73c38ba44ad8ce85d8351085f2f
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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