Hydrochloric Acid → HCID 58960222, compound

HRID 916424Notes

Reaction equation

HRID 916424 reaction equation
[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH2:25][C@H:26]4[CH2:30][CH2:29][CH2:28][N:27]4C(OC(C)(C)C)=O)=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:38])[NH:6]2.Cl>O1CCOCC1.CO>[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH2:25][C@H:26]4[CH2:30][CH2:29][CH2:28][NH:27]4)=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:38])[NH:6]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67019236HCID 67019236, compound

Product 1

HCID 58960222HCID 58960222, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Using an analogous procedure to that described for the preparation of the starting material in Example 11, tert-butyl (2R)-2-[(4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinazolin-7-yloxy)methyl]pyrrolidine-1-carboxylate (960 mg, 1.84 mmol) was reacted with hydrogen chloride in dioxane. The solid was dissolved in methanol and absorbed onto an Isolute SCX column which was washed through with methanol and then the product was eluted with 7N ammonia in methanol to give 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-[(2R)-pyrrolidin-2-ylmethoxy]quinazoline (480 mg, 62%).

Workup

  1. customabsorbed onto an Isolute SCX column which
  2. washwas washed through with methanol
  3. washthe product was eluted with 7N ammonia in methanol

Sources & evidence

ORD record
ord-ab111b15e18f4a21953f3e2c54f43cfb
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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