N,N-Dimethylaniline → HCID 22472971, compound

HRID 2183741Notes

Reaction equation

HRID 2183741 reaction equation
C([O:3][C:4](=O)[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]([CH3:28])[N:23]=[CH:22]3)=[CH:16][CH:17]=1)[C:6](OCC)=[O:7])C.NC1C=C[C:34]([O:37]C2C=C3C(=CC=2)N(C)N=C3)=[N:35]C=1.BrCC[C:51]([CH2:58][CH3:59])(C([O-])=O)C([O-])=O.C[N:61](C)C1C=CC=CC=1>>[CH3:28][N:24]1[C:25]2[C:21](=[CH:20][C:19]([O:18][C:15]3[N:14]=[CH:13][C:12]([N:11]4[C:5]5([C:6](=[O:7])[NH:61][C:34](=[O:37])[NH:35][C:4]5=[O:3])[CH2:51][CH2:58][CH2:59]4)=[CH:17][CH:16]=3)=[CH:27][CH:26]=2)[CH:22]=[N:23]1

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 22472978HCID 22472978, compoundHCID 69704432HCID 69704432, compoundHCID 131724956HCID 131724956, compound

Product 1

HCID 22472971HCID 22472971, compound

Conditions

Temperature
70 °C

Procedure

2-[6-(1-Methyl-1H-indazol-5-yloxy)-pyridin-3-ylamino]-malonic acid diethyl ester can be prepared by combining 5-(5-Amino-pyridin-2-yloxy)-1-methyl-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-1ce012054dae4da6acba5dc42fc2a718
Source dataset
uspto-grants-2005_05
Patent number
US06900201B2

Reaction notes

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