Phenacyl bromide → HCID 59563707, compound

HRID 1944163Notes

Reaction equation

HRID 1944163 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]([NH:20][C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[N:26][CH:25]=[CH:24]3)=[O:19])[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:34][C:35]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:36]>CN(C=O)C>[CH:27]1[C:28]2[C:23](=[CH:22][C:21]([NH:20][C:18](=[O:19])[CH:8]([C:5]3[CH:6]=[CH:7][C:2]([O:1][CH2:34][C:35](=[O:36])[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:3][CH:4]=3)[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[CH:30][CH:29]=2)[CH:24]=[CH:25][N:26]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 24758Sodium hydrideHCID 59563693HCID 59563693, compound

Product 1

HCID 59563707HCID 59563707, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-35 °C

Procedure

To tert-butyl 2-(4-hydroxyphenyl)-3-(isoquinolin-6-ylamino)-3-oxopropylcarbamate (E249) in DMF cooled to −35° C. was added NaH and the solution was stirred at −35° C. for 30 min. Then, 2-bromoacetophenone was added and the solution was warmed and stirred at 0° C. for 2 h. The solution was poured into NaHCO3(sat)/EtOAc and further extracted with EtOAc. The combined organics were dried (Na2SO4), filtered, and evaporated. Column chromatography (SiO2, 3% MeOH/CH2Cl2) gave tert-butyl 3-(isoquinolin-6-ylamino)-3-oxo-2-(4-(2-oxo-2-phenylethoxy)phenyl)propylcarbamate (E275).

Workup

  1. temperaturethe solution was warmed
  2. stirringstirred at 0° C. for 2 h
  3. extractionfurther extracted with EtOAc
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-477251db6ed3437799a2e0316b69e91a
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

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