Dimethylformamide → HCID 68212999, compound

HRID 2089631

Reaction equation

HRID 2089631 reaction equation
[NH2:1][C:2](=[N:36][C:37](=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:23]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[C:25]([O:31][CH2:32][CH2:33][OH:34])[C:24]=2[F:35])[C:11]2[NH:15][C:14](=[O:16])[N:13]([C:17]3[N:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[N:12]=2)=[CH:5][CH:4]=1.CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:57][O:58][C:59](=[O:66])[C:60]([CH3:65])([CH3:64])[CH2:61][O:62][CH3:63]>O.C(OCC)(=O)C>[NH2:1][C:2](=[N:36][C:37](=[O:44])[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:23]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[C:25]([O:31][CH2:32][CH2:33][OH:34])[C:24]=2[F:35])[C:11]2[N:15]=[C:14]([O:16][CH2:57][O:58][C:59](=[O:66])[C:60]([CH3:65])([CH3:64])[CH2:61][O:62][CH3:63])[N:13]([C:17]3[N:18]=[CH:19][CH:20]=[CH:21][N:22]=3)[N:12]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 144596933-Methoxy-2,2-dimethylpropionic acid chloromethyl esterHCID 136334022N-[1-amino-1-(4-{[[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}phenyl)methylidene]benzamide

Product 1

HCID 68212999HCID 68212999, compoundYield 35.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of N-[1-amino-1-(4-{[[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}phenyl)methylidene]benzamide (Example 1a, 45 mg) and DMF (2 mL), cesium carbonate (29 mg) and 3-methoxy-2,2-dimethylpropionic acid chloromethyl ester (20 mg) were sequentially added, and the resulting mixture was stirred at 60° C. for 4 hours. The resulting mixture was poured into ethyl acetate (30 mL) and water (20 mL). After shaking the mixture, the organic layer was collected. The organic layer was sequentially washed twice with water (30 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 (20 mg).

Workup

  1. additionwere sequentially added
  2. stirringAfter shaking the mixture
  3. customthe organic layer was collected
  4. washThe organic layer was sequentially washed twice with water (30 mL) and with saturated aqueous sodium chloride solution (20 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe resulting mixture was filtered
  7. customthe filtrate obtained
  8. concentrationwas concentrated under reduced pressure
  9. customThe residue obtained
  10. customwas purified by NAM silica gel column chromatography (mixed solvent of methanol-ethyl acetate)

Sources & evidence

ORD record
ord-527ceb6ba360489dacf24700108e7804
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Linked notes

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