N,N-Dimethylaniline → HCID 10096218, compound

HRID 2183736Notes

Reaction equation

HRID 2183736 reaction equation
C(O[C:4](=[O:34])[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:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[N:23]=[CH:22]3)=[CH:16][CH:17]=1)[C:6](OCC)=[O:7])C.NC1C=C[C:39]([O:42]C2C=C3C(=CC=2)N(C2C=NC=CC=2)N=C3)=[N:40]C=1.BrCC[C:61]([CH2:68][CH3:69])(C([O-])=O)C([O-])=O.C[N:71](C)C1C=CC=CC=1>>[N:30]1[CH:31]=[CH:32][CH:33]=[C:28]([N:24]2[C:25]3[C:21](=[CH:20][C:19]([O:18][C:15]4[N:14]=[CH:13][C:12]([N:11]5[C:5]6([C:6](=[O:7])[NH:71][C:39](=[O:42])[NH:40][C:4]6=[O:34])[CH2:61][CH2:68][CH2:69]5)=[CH:17][CH:16]=4)=[CH:27][CH:26]=3)[CH:22]=[N:23]2)[CH:29]=1

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 22472954HCID 22472954, compoundHCID 69704688HCID 69704688, compoundHCID 131724956HCID 131724956, compound

Product 1

HCID 10096218HCID 10096218, compound

Conditions

Temperature
70 °C

Procedure

2-[6-(1-Pyridin-3-yl-1H-indazol-5-yloxy)-pyridin-3-ylamino]-malonic acid diethyl ester can be prepared by combining 5-(5-Amino-pyridin-2-yloxy)-1-pyridin-3-yl-1H-indazole (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-0ab6e346828443a1ae947f3e4e4172fc
Source dataset
uspto-grants-2005_05
Patent number
US06900201B2

Reaction notes

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