1-Bromohexane → HCID 68419578, compound

HRID 927329Notes

Reaction equation

HRID 927329 reaction equation
[C:1]([O:5][C:6](=[O:43])[N:7]([CH2:28][CH2:29][CH2:30][N:31]1[C:40](=[O:41])[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][C:32]1=[O:42])[CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][CH2:15][N:16]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][C:17]1=[O:27])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]>O1CCCC1>[C:1]([O:5][C:6](=[O:43])[N:7]([CH2:28][CH2:29][CH2:30][N:31]1[C:40](=[O:41])[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][C:32]1=[O:42])[CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH2:14][CH2:15][N:16]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][C:17]1=[O:27])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 68418633HCID 68418633, compound

Product 1

HCID 68419578HCID 68419578, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[3-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)propyl]-{4-[3-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)propylamino]butyl}carbamic acid tert-butyl ester (2 g, 3.4 mmol) was dissolved in 40 mL tetrahydrofuran. Sodium hydride (0.16 g, 6.7 mmol) and 1-bromohexane (0.67 g, 4.0 mmol) were added thereto and stirred under reflux. The solvent was concentrated under reduced pressure, and silica gel column-chromatography of the remaining residue was performed to give the title compound of white solid (0.52 g, 23%).

Workup

  1. temperatureunder reflux
  2. concentrationThe solvent was concentrated under reduced pressure, and silica gel column-chromatography of the remaining residue

Sources & evidence

ORD record
ord-71296ebdb78b4f089218727e9e88af2a
Source dataset
uspto-grants-2016_03
Patent number
US09290480B2

Reaction notes

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