N,N-Dimethylaniline → HCID 10480845, compound

HRID 2183731Notes

Reaction equation

HRID 2183731 reaction equation
C(O[C:4](=[O:36])[CH:5]([NH:11][C:12]1[CH:13]=[N:14][C:15]([O:18][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24]([C:28]2[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=2)[N:23]=[CH:22]3)=[CH:16][CH:17]=1)[C:6](OCC)=[O:7])C.NC1C=C[C:41]([O:44]C2C=C3C(=CC=2)N(C2C=CC(C#N)=CC=2)N=C3)=[N:42]C=1.BrCC[C:65]([CH2:72][CH3:73])(C([O-])=O)C([O-])=O.C[N:75](C)C1C=CC=CC=1>>[O:7]=[C:6]1[NH:75][C:41](=[O:44])[NH:42][C:4](=[O:36])[C:5]21[N:11]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[N:24]([C:28]3[CH:29]=[CH:30][C:31]([C:34]#[N:35])=[CH:32][CH:33]=3)[N:23]=[CH:22]4)=[N:14][CH:13]=1)[CH2:65][CH2:72][CH2:73]2

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 22472958HCID 22472958, compoundHCID 69704846HCID 69704846, compoundHCID 131724956HCID 131724956, compound

Product 1

HCID 10480845HCID 10480845, compound

Conditions

Temperature
70 °C

Procedure

2-{6-[1-(4-Cyano-phenyl)-1H-indazol-5-yloxy]-pyridin-3-ylamino}-malonic acid diethyl ester can be prepared by combining 4-[5-(5-Amino-pyridin-2-yloxy)-indazol-1-yl]-benzonitrile (11.4 mmol), bromodiethylmalonate (11.4 mmol), and N,N-dimethylaniline (11.4 mmol) in a flame dried flask and heated to 70° C. for 3.5 hours. The mixture is cooled to room temperature, adsorbed to silica gel and chromatographed (gradient elution, ethyl acetate-hexanes) to afford the title compound.

Workup

  1. customdried flask
  2. temperatureThe mixture is cooled to room temperature
  3. customchromatographed
  4. wash(gradient elution, ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-a61c0d16b28b406abbbee229277fe988
Source dataset
uspto-grants-2005_05
Patent number
US06900201B2

Reaction notes

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