Dimethylformamide → HCID 68212843, compound

HRID 2089660Notes

Reaction equation

HRID 2089660 reaction equation
[NH2:1][C:2](=[N:44][C:45](=[O:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:32]2[NH:36][C:35](=[O:37])[N:34]([C:38]3[N:43]=[CH:42][CH:41]=[CH:40][N:39]=3)[N:33]=2)[C:11]2[C:12]([F:31])=[C:13]([CH:26]=[C:27]([O:29][CH3:30])[CH:28]=2)[O:14][CH2:15][CH2:16][O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)=[CH:5][CH:4]=1.Cl[CH2:54][O:55][C:56](=[O:61])[C:57]([CH3:60])([CH3:59])[CH3:58].C(=O)([O-])O.[K+].CN(C=O)C>O.C(OCC)(=O)C>[NH2:1][C:2](=[N:44][C:45](=[O:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH:10]([C:32]2[N:36]=[C:35]([O:37][CH2:54][O:55][C:56](=[O:61])[C:57]([CH3:60])([CH3:59])[CH3:58])[N:34]([C:38]3[N:39]=[CH:40][CH:41]=[CH:42][N:43]=3)[N:33]=2)[C:11]2[C:12]([F:31])=[C:13]([CH:26]=[C:27]([O:29][CH3:30])[CH:28]=2)[O:14][CH2:15][CH2:16][O:17][C:18](=[O:25])[C:19]2[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 87885Chloromethyl pivalateHCID 516893Potassium BicarbonateHCID 136334030HCID 136334030, compound

Product 1

HCID 68212843HCID 68212843, compoundYield 33.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

Under nitrogen atmosphere, a mixture of isonicotinic acid 2-{3-[(4-{amino[benzoylimino]methyl}phenylamino)-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]-2-fluoro-5-methoxyphenoxy}ethyl ester (31.3 mg), 2,2-dimethylpropionic acid chloromethyl ester (9.1 mg), potassium hydrogen carbonate (6.7 mg), and DMF (2 mL) was stirred at 45° C. for 20 hours. The mixture was poured into ethyl acetate (100 mL) and water (20 mL). After shaking the mixture, the organic layer was collected, sequentially washed three times with water (20 mL) and with saturated aqueous sodium chloride solution (20 mL), and dried over anhydrous magnesium sulfate. The resulting mixture was filtered, and the filtrate obtained was concentrated under reduced pressure. The residue obtained was purified by NAM silica gel column chromatography (mixed solvent of methanol-ethyl acetate) to obtain the captioned compound (12.2 mg).

Workup

  1. stirringAfter shaking the mixture
  2. customthe organic layer was collected
  3. washsequentially washed three times with water (20 mL)
  4. dry with materialwith saturated aqueous sodium chloride solution (20 mL), and dried over anhydrous magnesium sulfate
  5. filtrationThe resulting mixture was filtered
  6. customthe filtrate obtained
  7. concentrationwas concentrated under reduced pressure
  8. customThe residue obtained
  9. customwas purified by NAM silica gel column chromatography (mixed solvent of methanol-ethyl acetate)

Sources & evidence

ORD record
ord-0e8fb3ab222f440b87bc94bf997a795c
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Reaction notes

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