1-Boc-4-(3-hydroxypropyl)piperazine → HCID 67019221, compound

HRID 916428Notes

Reaction equation

HRID 916428 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][OH:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:18][C:19]1[C:27]([O:28][C:29]2[C:38]3[C:33](=[CH:34][C:35](O)=[C:36]([O:39][CH3:40])[CH:37]=3)[N:32]=[CH:31][N:30]=2)=[CH:26][CH:25]=[C:24]2[C:20]=1[CH:21]=[C:22]([CH3:42])[NH:23]2>>[F:18][C:19]1[C:27]([O:28][C:29]2[C:38]3[C:33](=[CH:34][C:35]([O:17][CH2:16][CH2:15][CH2:14][N:11]4[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][CH2:12]4)=[C:36]([O:39][CH3:40])[CH:37]=3)[N:32]=[CH:31][N:30]=2)=[CH:26][CH:25]=[C:24]2[C:20]=1[CH:21]=[C:22]([CH3:42])[NH:23]2

Participants

3

Reactant 2

HCID 162178001-Boc-4-(3-hydroxypropyl)piperazineHCID 1355308324-((4-Fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-ol

Product 1

HCID 67019221HCID 67019221, compoundYield 70%

Procedure

Using an analogous procedure to that described for the preparation of the starting material in Example 11, 1-tert-butoxycarbonyl-4-(3-hydroxypropyl)piperazine (432 mg, 1.77 mmol) was reacted with 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-7-hydroxy-6-methoxyquinazoline (500 mg, 1.47 mmol), (prepared as described for the starting material in Example 7). The product was purified by column chromatography, eluting with 2%-5% methanol/methylene chloride to give tert-butyl 4-[3-(4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinazoline-7-yloxy)propyl]piperazine-1-carboxylate (582 mg, 70%).

Workup

  1. custom(prepared
  2. customThe product was purified by column chromatography
  3. washeluting with 2%-5% methanol/methylene chloride

Sources & evidence

ORD record
ord-28f060e4b960491eb9c7601138f22db6
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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