Methanesulfonyl chloride → HCID 10311487, compound

HRID 2068074Notes

Reaction equation

HRID 2068074 reaction equation
C(N(C(C)C)CC)(C)C.[CH3:10][S:11](Cl)(=[O:13])=[O:12].[F:15][C:16]1[C:24]([O:25][C:26]2[C:35]3[C:30](=[CH:31][C:32]([O:38][CH2:39][CH:40]4[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]4)=[C:33]([O:36][CH3:37])[CH:34]=3)[N:29]=[CH:28][N:27]=2)=[CH:23][CH:22]=[C:21]2[C:17]=1[CH:18]=[C:19]([CH3:46])[NH:20]2>C(Cl)Cl>[F:15][C:16]1[C:24]([O:25][C:26]2[C:35]3[C:30](=[CH:31][C:32]([O:38][CH2:39][CH:40]4[CH2:45][CH2:44][N:43]([S:11]([CH3:10])(=[O:13])=[O:12])[CH2:42][CH2:41]4)=[C:33]([O:36][CH3:37])[CH:34]=3)[N:29]=[CH:28][N:27]=2)=[CH:23][CH:22]=[C:21]2[C:17]=1[CH:18]=[C:19]([CH3:46])[NH:20]2

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 589602204-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-(piperidin-4-ylmethoxy)quinazoline

Product 1

HCID 10311487HCID 10311487, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropylethylamine (72 μl, 0.41 mmol) and methanesulphonyl chloride (32 μl, 0.41 mmol) were added to a suspension of 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-(piperidin-4-ylmethoxy)quinazoline (150 mg, 0.34 mmol), (prepared as described for the starting material in Example 11), in methylene chloride (4 ml). After a few minutes all the material had gone into solution. The mixture was stirred for 3 hours at ambient temperature, washed with saturated sodium hydrogen carbonate solution, dried (MgSO4) and concentrated under reduced pressure. The solid was suspended in methanol and filtered to give 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-{[1-(methylsulfonyl)piperidin-4-yl]methoxy}quinazoline (83 mg, 47%).

Workup

  1. custom(prepared
  2. waitAfter a few minutes all the material had gone into solution
  3. washwashed with saturated sodium hydrogen carbonate solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. filtrationfiltered

Sources & evidence

ORD record
ord-ac903ec8ee944fc597e8520258292fe7
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

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