Ethyl Bromide → HCID 68115357, compound

HRID 1503900Notes

Reaction equation

HRID 1503900 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:15][CH2:14][C:13]2[S:12][C:11]3[N:10]=[CH:9][N:8]=[C:7]([O:16][CH:17]4[CH2:22][CH2:21][CH:20]([N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:19][CH2:18]4)[C:6]=3[C:5]1=2.[H-].[Na+].Br[CH2:35][CH3:36]>CN(C=O)C>[CH2:35]([O:1][CH2:2][CH2:3][CH:4]1[CH2:15][CH2:14][C:13]2[S:12][C:11]3[N:10]=[CH:9][N:8]=[C:7]([O:16][CH:17]4[CH2:18][CH2:19][CH:20]([N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:21][CH2:22]4)[C:6]=3[C:5]1=2)[CH3:36]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 68115432HCID 68115432, compound

Product 1

HCID 68115357HCID 68115357, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 25-mL round-bottom flask was added a solution of intermediate 18.3 (125 mg, 0.28 mmol, 1.00 equiv) in distilled DMF (10 mL) followed by sodium hydride (60% dispersion in mineral oil, 96 mg, 2.80 mmol) at 0° C. and the reaction mixture was stirred for 30 min. Then bromoethane (305 mg, 2.80 mmol) was added and the resulting solution was stirred overnight at room temperature. The reaction was then quenched with water and extracted with 100 mL of ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was loaded onto a silica gel column with EtOAc/petroleum ether (1:5). Purification afforded tert-butyl N-(4-[[3-(2-ethoxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (19.1, 19 mg, 14%) as a colorless oil.

Workup

  1. stirringthe resulting solution was stirred overnight at room temperature
  2. customThe reaction was then quenched with water
  3. extractionextracted with 100 mL of ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customPurification

Sources & evidence

ORD record
ord-57f99c7d286f46218dfa7ca9f3d5d641
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

Loading…