Sodium → HCID 44193179, compound

HRID 1855415Notes

Reaction equation

HRID 1855415 reaction equation
[Na].Cl[C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]3)=[C:13]([O:23][CH3:24])[CH:12]=2)[N:4]=1>C(O)(C)C>[CH:13]([O:23][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]3)=[C:13]([O:23][CH3:24])[CH:12]=2)[N:4]=1)([CH3:14])[CH3:12]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 57829826HCID 57829826, compound

Product 1

HCID 44193179HCID 44193179, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Sodium (10 mg, 0.45 mmol) was dissolved under heating and stirring under an atmosphere of nitrogen in isopropanol (1 mL). (4-Chloro-6-methyl-pyrimidin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine (99 mg, 0.3 mmol) was added and the suspension was heated to reflux over night. The solvent was evaporated under reduced pressure and the residue was taken up in water and extracted twice with diethyl ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure to dryness. The residue was purified by column chromatography on silica gel using dichloromethane/methanol (19:1 v/v) as eluent. The fraction containing the product was purified by reversed preparative HPLC using acetonitril/water (0.1% formic acid) to yield the title compound as an off-white solid (25 mg, 24%). MS ISP (m/e): 354.2 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.73 (s, 1H), 7.63 (s, 1H), 7.18 (d, 1H), 7.04 (s, 1H), 7.03 (d, 1H), 6.87 (s, 1H), 6.06 (s, 1H), 5.36 (sept, 1H), 3.86 (s, 3H), 2.33 (s, 3H), 2.30 (s, 3H), 1.38 (s, 3H), 1.36 (s, 3H).

Workup

  1. temperatureunder heating
  2. temperaturethe suspension was heated
  3. temperatureto reflux over night
  4. customThe solvent was evaporated under reduced pressure
  5. extractionextracted twice with diethyl ether
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure to dryness
  10. customThe residue was purified by column chromatography on silica gel
  11. additionThe fraction containing the product
  12. customwas purified by reversed preparative HPLC

Sources & evidence

ORD record
ord-f5cffe2736484eab9c7f9c77c90197b1
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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