Potassium Carbonate → HCID 58277434, compound

HRID 1949225Notes

Reaction equation

HRID 1949225 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=3)=[CH:11][C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:31]([O:34][CH2:35][CH2:36][CH2:37]Br)(=[O:33])[CH3:32]>CN(C=O)C>[C:31]([O:34][CH2:35][CH2:36][CH2:37][O:19][C:15]1[CH:14]=[C:13]([C:12]2[N:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[N:9]=[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:11]=2)[CH:18]=[CH:17][CH:16]=1)(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122357751-Propanol, 3-bromo-, 1-acetateHCID 58277403HCID 58277403, compound

Product 1

HCID 58277434HCID 58277434, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

100 mg (0.292 mmol) of the compound of Example 44A are provided in 1 ml of dry DMF, 242 mg (1.75 mmol) of potassium carbonate and 158 mg (0.875 mmol) of 1-acetoxy-3-bromopropane are added, and the mixture is stirred at 90° C. for 4 h. The reaction mixture is subsequently purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with the addition of 0.1% formic acid) and 109 mg (84% of theory) of the title compound are obtained.

Workup

  1. customThe reaction mixture is subsequently purified by preparative HPLC (RP18 column
  2. additionmobile phase: acetonitrile/water gradient with the addition of 0.1% formic acid) and 109 mg (84% of theory) of the title compound
  3. customare obtained

Sources & evidence

ORD record
ord-966fe6118a2042e798728aa9a0cb331c
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

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