Formic Acid → 4-{5,7-Dimethyl-4-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-2-yl}phenylformamide

HRID 1270321Notes

Reaction equation

N1C=CN=C1.C(N(CC)CC)C.[CH:13]([OH:15])=O.C(Cl)(=O)C(Cl)=O.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[N:34]=[C:33]([NH:35][C:36]3[CH:41]=[C:40]([O:42][CH3:43])[C:39]([O:44][CH3:45])=[C:38]([O:46][CH3:47])[CH:37]=3)[C:32]3=[C:48]([CH3:52])[N:49]=[C:50]([CH3:51])[N:31]3[N:30]=2)=[CH:25][CH:24]=1>ClCCl>[CH3:52][C:48]1[N:49]=[C:50]([CH3:51])[N:31]2[C:32]=1[C:33]([NH:35][C:36]1[CH:37]=[C:38]([O:46][CH3:47])[C:39]([O:44][CH3:45])=[C:40]([O:42][CH3:43])[CH:41]=1)=[N:34][C:29]([C:26]1[CH:25]=[CH:24][C:23]([NH:22][CH:13]=[O:15])=[CH:28][CH:27]=1)=[N:30]2

Participants

Conditions

Temperature: 0 °C

Procedure

16 mg (0.24 mmol) of imidazole, 48 mg (0.48 mmol) of triethylamine and 11 mg (0.24 mmol) of formic acid are introduced into 4 ml dichloromethane under argon, cooled to 0° C. and treated dropwise with a solution of 30 mg (0.24 mmol) of oxalyl dichloride in dichloromethane. The mixture is allowed to warm to 20° C. and subsequently 100 mg (0.24 mmol) of N-[2-(4-aminophenyl)-5,7-dimethyl-imidazo[5,1-f][1,2,4]triazin-4-yl]-N-(3,4,5-trimethoxyphenyl)amine from example 3 are added thereto. It is stirred overnight and then washed with aqueous sodium hydrogencarbonate solution. The organic phase is dried and purified by flash chromatography (dichloromethane/methanol 100:1).

Workup

temperatureto warm to 20° C.
washwashed with aqueous sodium hydrogencarbonate solution
customThe organic phase is dried
custompurified by flash chromatography (dichloromethane/methanol 100:1)

Sources & evidence

ORD record: ord-9ccbcc4ca66d46e88b9465a906a16e07
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202243B2

Reaction notes

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