(+-)-2-Butanol → N-(5-(7-Methoxyquinolin-4-ylamino)pyrimidin-2-yl)benzamide

HRID 1042838Notes

Reaction equation

HRID 1042838 reaction equation
Cl[C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1N=[CH:9][C:8]([O:12][CH3:13])=[CH:7]2.[NH2:14][C:15]1[CH:16]=[N:17][C:18]([NH:21][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:19][CH:20]=1.[C:30]1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CC(O)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:14][C:15]3[CH:16]=[N:17][C:18]([NH:21][C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[N:19][CH:20]=3)=[CH:3][CH:4]=[N:5]2)=[CH:30][CH:9]=1

Participants

7

Reactant 5

HCID 6568(+-)-2-ButanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 11499482N-(5-aminopyrimidin-2-yl)benzamideHCID 594273408-Chloro-3-methoxy-1,5-naphthyridine

Product 1

HCID 67316087N-(5-(7-Methoxyquinolin-4-ylamino)pyrimidin-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

In a screw cap test tube were dissolved 8-chloro-3-methoxy-1,5-naphthyridine (281 mg, 1443 μmol), N-(5-aminopyrimidin-2-yl)benzamide (281 mg, 1312 μmol) and pyridinium p-toluenesulfonate (494 mg, 1968 μmol) in butan-2-ol (2623 μl, 1312 μmol) then heated at 100° C. The reaction turned black in a minute. After 1 h, the reaction mixture showed full conversion to product according to LCMS. The reaction mixture was diluted with CH2Cl2, neutralized with sat. NaHCO3. An emulsion was formed but the two layers eventually separated. The aqueous phase was extracted 3 times with CH2Cl2, washed with brine, dried over MgSO4, filtered and evaporated under reduce pressure to give a tan solid. The solid was triturated with hexane, filtered, and dried under vacuo. Brown solid was collected. LCMS confirmed the presence of the product, N-(5-(7-methoxy-1,5-naphthyridin-4-ylamino)pyrimidin-2-yl)benzamide. MS Calcd for C20H16N6O2: [M]+=372. Found: [M+H]+=373.

Workup

  1. customIn a screw cap test tube
  2. customAn emulsion was formed
  3. customthe two layers eventually separated
  4. extractionThe aqueous phase was extracted 3 times with CH2Cl2
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give a tan solid
  10. customThe solid was triturated with hexane
  11. filtrationfiltered
  12. customdried under vacuo
  13. customBrown solid was collected

Sources & evidence

ORD record
ord-5387c350e6854dd1b4b142a03ffc720b
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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