Methanesulfonic Acid → HCID 15549984, compound

HRID 431020Notes

Reaction equation

HRID 431020 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 of 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 of 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 diethylether 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-53f605fef8f743a49ad3740bdfeed76b
Source dataset
uspto-grants-2003_12
Patent number
US06656946B2

Reaction notes

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