Isopropanol → HCID 69201258, compound

HRID 2117650Notes

Reaction equation

HRID 2117650 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][O:8][C:9](=[O:28])[N:10]([C:21]2[CH:26]=[CH:25][N:24]=[C:23](Cl)[N:22]=2)[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=2[O:19][CH3:20])[CH:2]=1.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:35]=[CH:36][C:37]=1[N:38]1[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]1)[NH2:34].C(O)(C)C.FC(F)(F)C(O)=O>C(OCC)(=O)C>[CH3:20][O:19][C:12]1[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:11]=1[N:10]([C:21]1[CH:26]=[CH:25][N:24]=[C:23]([NH:34][C:33]2[CH:35]=[CH:36][C:37]([N:38]3[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]3)=[C:31]([O:30][CH3:29])[CH:32]=2)[N:22]=1)[C:9](=[O:28])[O:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 6422Trifluoroacetic acidHCID 118447613-Methoxy-4-(4-methylpiperazin-1-yl)anilineHCID 86596308HCID 86596308, compound

Product 1

HCID 69201258HCID 69201258, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A resealable tube was charged with (2-chloro-pyrimidin-4-yl)-(2,4-dimethoxy-phenyl)carbamic acid pyridin-3-ylmethyl ester (0.100 g, 0.249 mol), 3-(methyloxy)-4-(4-methyl-1-piperazinyl)aniline (0.100 g, 0.45 mmol), and isopropanol (2 mL). Trifluoroacetic acid (0.074 g, 0.050 mL, 0.65 mmol) was added. The tube was sealed and the mixture was heated at 60° C. for 20 h. The reaction mixture was cooled to room temperature and concentrated to afford a pale purple oil. The resulting solution was diluted with ethyl acetate and the mixture was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was separated, dried over anhydrous sodium sulfate, filtered, and concentrated to afford an oil. This oil was purified via column chromatography on silica gel (gradient elution with 0-100% dichloromethane-(90:10:1, dichloromethane/methanol/ammonium hydroxide)) to afford 3-pyridinylmethyl 2,4-bis(methyloxy)-phenyl(2-((3-(methyloxy)-4-(4-methyl-1-piperazinyl)phenyl)amino)-4-pyrimidinyl)-carbamate as an off-white solid. MS (MH+) 586; Calculated 585.66 for C31H35N7O5.

Workup

  1. customThe tube was sealed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated
  4. customto afford a pale purple oil
  5. customthe mixture was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  6. customThe organic phase was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford an oil
  11. customThis oil was purified via column chromatography on silica gel (gradient elution with 0-100% dichloromethane-(90:10:1, dichloromethane/methanol/ammonium hydroxide))

Sources & evidence

ORD record
ord-e253d150083646cab333c8513e0f2989
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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