Potassium Carbonate → N-(1-ethynyl-cyclobutyl)-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide

HRID 1962888Notes

Reaction equation

HRID 1962888 reaction equation
[CH3:1]OP(C(=[N+]=[N-])C(=O)C)(=O)OC.[C:13]([C:15]1[CH:16]=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][C:21]([O:25][CH:26]([S:36][CH3:37])[C:27]([NH:29][C:30]1([CH:34]=O)[CH2:33][CH2:32][CH2:31]1)=[O:28])=[CH:20][CH:19]=2)#[CH:14].C(=O)([O-])[O-].[K+].[K+]>CO.[Cl-].[Na+].O>[C:34]([C:30]1([NH:29][C:27](=[O:28])[CH:26]([O:25][C:21]2[CH:22]=[C:23]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][C:15]([C:13]#[CH:14])=[CH:24]3)[S:36][CH3:37])[CH2:33][CH2:32][CH2:31]1)#[CH:1]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 595654712-(3-ethynyl-quinolin-6-yloxy)-N-(1-formyl-cyclobutyl)-2-methylsulfanyl-acetamideHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 59565355N-(1-ethynyl-cyclobutyl)-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Bestmann's reagent ((1-diazo-2-oxo-propyl)-phosphonic acid dimethyl ester) (123 mg) was added to a solution of 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-formyl-cyclobutyl)-2-methylsulfanyl-acetamide (180 mg) from Step 2 above in MeOH (15 ml) under nitrogen atmosphere. After cooling to 0° C. potassium carbonate (114 mg) was added and the mixture was stirred overnight at temperature from 0° C. to room temperature, then poured into brine and extracted with ethyl acetate (2×). The combined organic layers were washed with water, dried over sodium sulphate anhydrous, filtered and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate/CH2Cl2, 1/1/3) to give N-(1-ethynyl-cyclobutyl)-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide (106 mg) as white solid.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate (2×)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over sodium sulphate anhydrous
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate/CH2Cl2, 1/1/3)

Sources & evidence

ORD record
ord-61593aafa38f4b7b96f8e2a959a98796
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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