Sodium hydride → HCID 5276094, compound

HRID 1788441Notes

Reaction equation

HRID 1788441 reaction equation
C[O:2][C:3]([C:5]1[CH:43]=[CH:42][C:8]2[N:9]([CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)[C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[C:17]([C:22]3[C:27]([C:28]5[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=5)=[CH:26][CH:25]=[C:24]([OH:35])[CH:23]=3)[CH:16]=[CH:15]4)=[N:11][C:7]=2[CH:6]=1)=[O:4].[H-].[Na+].Br[CH2:47][CH2:48][O:49][CH3:50]>CN(C=O)C>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([C:27]2[C:22]([C:17]3[CH:16]=[CH:15][C:14]4[C:19](=[CH:20][CH:21]=[C:12]([C:10]5[N:9]([CH:36]6[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]6)[C:8]6[CH:42]=[CH:43][C:5]([C:3]([OH:2])=[O:4])=[CH:6][C:7]=6[N:11]=5)[CH:13]=4)[N:18]=3)=[CH:23][C:24]([O:35][CH2:47][CH2:48][O:49][CH3:50])=[CH:25][CH:26]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 131727377HCID 131727377, compound

Product 1

HCID 5276094HCID 5276094, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 475a (100 mg, 0.162 mmol) was dissolved in 2 mL of DMF and treated with 16.8 mg (0.7 mmol) of NaH for 30 min. 1-bromo-2-methoxy ethane (30.5 μL) was added and the mixture was agitated overnight. The next day the reaction mixture was evaporated to dryness, the oily residue dissolved in 3 mL methanol followed by the addition of 1 mL 1M NaOH. The mixture was refluxed for 2 h before it was evaporated to dryness. The product was purified by RP-HPLC for a yield of 19.3 mg of the title compound.

Workup

  1. customThe next day the reaction mixture was evaporated to dryness
  2. dissolutionthe oily residue dissolved in 3 mL methanol
  3. additionfollowed by the addition of 1 mL 1M NaOH
  4. temperatureThe mixture was refluxed for 2 h before it
  5. customwas evaporated to dryness
  6. customThe product was purified by RP-HPLC for a yield of 19.3 mg of the title compound

Sources & evidence

ORD record
ord-7e214870f98549bea9cf3f9e96546682
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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