Methanesulfonic Acid → HCID 15549984, compound

HRID 502485Notes

Reaction equation

HRID 502485 reaction equation
CS(O)(=O)=O.[Br:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:40][CH3:41])=[C:21]([O:24][CH2:25][CH2:26][N:27]([CH2:32][C:33]([O:35][C:36](C)(C)[CH3:37])=[O:34])[CH2:28][C@@H](O)C)[CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1>C(#N)C.C(OCC)(=O)C>[Br:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:40][CH3:41])=[C:21]([O:24][CH2:25][CH2:26][N:27]4[CH2:28][C@H:36]([CH3:37])[O:35][C:33](=[O:34])[CH2:32]4)[CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 6395Methanesulfonic Acid2×HCID 20607320HCID 20607320, compound

Product 1

HCID 15549984HCID 15549984, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

90 μl methanesulphonic acid are added to 380 mg of 4-[(3-bromo-phenyl)amino]-6-(2-{N-[(tert.butyloxycarbonyl)methyl]-N-((S)-2-hydroxy-propyl)-amino}-ethoxy)-7-methoxy-quinazoline in 8 ml acetonitrile. The reaction mixture is refluxed for about three hours, then another equivalent of methanesulphonic acid is added and refluxing is continued until the reaction is complete. For working up the reaction mixture is diluted with ethyl acetate and washed with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution. The organic phase is dried over magnesium sulphate and evaporated down in vacuo. The flask residue is stirred with diethyl ether and suction filtered. The title compound is obtained as a white solid.

Workup

  1. temperatureThe reaction mixture is refluxed for about three hours
  2. temperaturerefluxing
  3. washwashed with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. customevaporated down in vacuo
  6. filtrationfiltered

Sources & evidence

ORD record
ord-43433f90903b4f07b118fa1e16cdd9a8
Source dataset
uspto-grants-2010_08
Patent number
US07776315B2

Reaction notes

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