Potassium Carbonate → HCID 9957955, compound

HRID 1953530Notes

Reaction equation

HRID 1953530 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23](=[O:33])/[CH:24]=[CH:25]/[C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=3)=[CH:4][C:3]=2[O:2]1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl.CO>CN(C=O)C>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23](=[O:33])/[CH:24]=[CH:25]/[C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:5][CH2:10][N:11]([CH3:23])[CH3:12])[CH:27]=3)=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 9911012HCID 9911012, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 9957955HCID 9957955, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 58 (0.25 g, 0.57 mmol) in 50 mL of DMF was added K2CO3 (0.24 g, 3 equiv.) and an excess of dimethylaminodiethyl chloride (about 15 equiv.). The resulting mixture was heated at 60° C. for four hours until disappearance of the starting material (tlc monitoring, DCM:MeOH (90:10). A new compound was formed (Rf=0.20). After evaporation of DMF, the residue was taken up in 150 mL of DCM, washed with 2×50 mL of water, dried over Na2SO4 and recrystallized from EtOH:H2O. to give the title compound (0.06 g, 22%) as yellow crystals.

Workup

  1. customA new compound was formed (Rf=0.20)
  2. customAfter evaporation of DMF
  3. washwashed with 2×50 mL of water
  4. dry with materialdried over Na2SO4
  5. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-eaa53e01d2a642bebf1685b85249bb3e
Source dataset
uspto-grants-2000_09
Patent number
US06117881

Reaction notes

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