N-(tert-Butoxycarbonyl)-D-prolinol → HCID 67019236, compound

HRID 2068065Notes

Reaction equation

HRID 2068065 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[F:15][C:16]1[C:24]([O:25][C:26]2[C:35]3[C:30](=[CH:31][C:32](O)=[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]([CH3:39])[NH:20]2>>[F:15][C:16]1[C:24]([O:25][C:26]2[C:35]3[C:30](=[CH:31][C:32]([O:1][CH2:2][C@H:3]4[CH2:7][CH2:6][CH2:5][N:4]4[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[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]([CH3:39])[NH:20]2

Participants

3

Reactant 2

HCID 688279N-(tert-Butoxycarbonyl)-D-prolinolHCID 1355308324-((4-Fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-ol

Product 1

HCID 67019236HCID 67019236, compoundYield 62.9%

Procedure

Using an analogous procedure to that described for the preparation of the starting material in Example 11, tert-butyl (2R)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (1.48 g, 7.37 mmol) was reacted with 4-(4-fluoro-2-methylindol-5-yloxy)-7-hydroxy-6-methoxyquinazoline (1.0 g, 2.95 mmol), (prepared as described for the starting material in Example 7), and the product purified by column chromatography, eluting with methanol/methylene chloride (1/9) containing 0.1% triethylamine to give tert-butyl (2R)-2-[(4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinazolin-7-yloxy)methyl]pyrrolidine 1-carboxylate (970 mg, 62%).

Workup

  1. custom(prepared
  2. custompurified by column chromatography
  3. washeluting with methanol/methylene chloride (1/9)
  4. additioncontaining 0.1% triethylamine

Sources & evidence

ORD record
ord-0cc94a29cc2f40728ee91c2044caea48
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

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