1,2-Dichloroethane → N-{4-[5,7-Dimethyl-4-(3,4,5-trimethoxyphenoxy)imidazo[5,1-f][1,2,4]triazin-2-yl]-phenyl}acetamide

HRID 1270311Notes

Reaction equation

HRID 1270311 reaction equation
[C:1]([OH:4])(=O)[CH3:2].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl.[CH3:26][C:27]1[N:28]=[C:29]([CH3:56])[N:30]2[C:35]=1[C:34]([O:36][C:37]1[CH:42]=[C:41]([O:43][CH3:44])[C:40]([O:45][CH3:46])=[C:39]([O:47][CH3:48])[CH:38]=1)=[N:33][C:32]([C:49]1[CH:55]=[CH:54][C:52]([NH2:53])=[CH:51][CH:50]=1)=[N:31]2>ClCCl>[CH3:26][C:27]1[N:28]=[C:29]([CH3:56])[N:30]2[C:35]=1[C:34]([O:36][C:37]1[CH:38]=[C:39]([O:47][CH3:48])[C:40]([O:45][CH3:46])=[C:41]([O:43][CH3:44])[CH:42]=1)=[N:33][C:32]([C:49]1[CH:50]=[CH:51][C:52]([NH:53][C:1](=[O:4])[CH3:2])=[CH:54][CH:55]=1)=[N:31]2

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 12095702HCID 12095702, compound

Product 1

HCID 10457109N-{4-[5,7-Dimethyl-4-(3,4,5-trimethoxyphenoxy)imidazo[5,1-f][1,2,4]triazin-2-yl]-phenyl}acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of 10 mg (0.09 mmol) of acetic acid in dichloromethane is treated with 10 mg (0.09 mmol) of HOBt and 20 mg (0.21 mmol) of 4-methylmorpholine. The mixture is cooled to −20° C. and treated with 20 mg (0.09 mmol) of EDC. It is stirred for 30 min. Subsequently, 30 mg (0.07 mmol) of 4-[5,7-dimethyl-4-(3,4,5-tri-methoxyphenoxy)imidazo[5,1-f][1,2,4]triazin-2-yl]aniline from example 1 are added thereto at −20° C., and the mixture is stirred for 5 h at 20° C. The solution is then washed with aqueous 1 N potassium hydrogensulfate solution and saturated aqueous sodium hydrogencarbonate solution. The organic phase is dried and concentrated under reduced pressure. The residue is purified by flash chromatography (eluent:dichloromethane/methanol 100:1-80:1-60:1).

Workup

  1. stirringat −20° C., and the mixture is stirred for 5 h at 20° C
  2. washThe solution is then washed with aqueous 1 N potassium hydrogensulfate solution and saturated aqueous sodium hydrogencarbonate solution
  3. customThe organic phase is dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by flash chromatography (eluent:dichloromethane/methanol 100:1-80:1-60:1)

Sources & evidence

ORD record
ord-f6355a64779e4acd9c2f65d68e5fa026
Source dataset
uspto-grants-2007_04
Patent number
US07202243B2

Reaction notes

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