1-Bromohexane → HCID 68420486, compound

HRID 927330Notes

Reaction equation

HRID 927330 reaction equation
[C:1]([O:5][C:6](=[O:50])[N:7]([CH2:23][CH2:24][CH2:25][CH2:26][N:27]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[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][N:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][C:12]1=[O:22])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63]>C(#N)C>[C:46]([O:45][C:43](=[O:44])[N:27]([CH2:26][CH2:25][CH2:24][CH2:23][N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:50])[CH2:8][CH2:9][CH2:10][N:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:18][CH2:19][CH2:14][CH2:15][CH2:16][CH3:17])[C:12]1=[O:22])[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)[N:33]([CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[C:32]1=[O:42])([CH3:49])([CH3:48])[CH3:47]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 68420575HCID 68420575, compound

Product 1

HCID 68420486HCID 68420486, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(4-{tert-butoxycarbonyl-[3-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)propyl]amino}butyl)-[3-(2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)propyl]carbamic acid tert-butyl ester (3 g, 4.3 mmol) was dissolved in 120 mL acetonitrile. Potassium carbonate (3.45 g, 25.0 mmol) and 1-bromohexane (3.5 g, 21.1 mmol) were added thereto and stirred for 3 hours 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 colorless oil form (3.7 g, 99%).

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-cbb5a424d8754bca9f274efb2d8c8714
Source dataset
uspto-grants-2016_03
Patent number
US09290480B2

Reaction notes

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