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

HRID 1962888노트

반응식

HRID 1962888 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 57417360Sodium chloride; water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-61593aafa38f4b7b96f8e2a959a98796
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415272B2

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