Sodium Bicarbonate → N-(1-dimethoxymethyl-cyclobutyl)-2-(3-ethynyl-quinolin-6-yloxy)-2methylsulfanyl-acetamide

HRID 1962890노트

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HRID 1962890 반응식
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:24][CH3:25])[C:15]([NH:17][C:18]1([CH:22]=[O:23])[CH2:21][CH2:20][CH2:19]1)=[O:16])=[CH:8][CH:7]=2)#[CH:2].C1(C)C=CC=CC=1.C1C[O:36][CH2:35]C1.[C:38]([O-])(O)=O.[Na+]>CO>[CH3:38][O:23][CH:22]([O:36][CH3:35])[C:18]1([NH:17][C:15](=[O:16])[CH:14]([O:13][C:9]2[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=2)[N:5]=[CH:4][C:3]([C:1]#[CH:2])=[CH:12]3)[S:24][CH3:25])[CH2:21][CH2:20][CH2:19]1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 22635083Tetrahydrofuran tolueneHCID 595654712-(3-ethynyl-quinolin-6-yloxy)-N-(1-formyl-cyclobutyl)-2-methylsulfanyl-acetamide

생성물 1

HCID 59565272N-(1-dimethoxymethyl-cyclobutyl)-2-(3-ethynyl-quinolin-6-yloxy)-2methylsulfanyl-acetamide

시약·촉매·용매 1

HCID 887Methanol용매

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온도
60 °C

실험 절차

To a solution of 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-formyl-cyclobutyl)-2-methylsulfanyl-acetamide (180 mg) from Example 12f, Step 2 described above in a 10/1 mixture of toluene/THF (11 ml) p-toluene sulphonic acid (4 mg) was added followed by MeOH (1.10 ml), at room temperature. The mixture was stirred at 50° C. overnight and 60° C. during 6 hrs, then after cooling to room temperature poured into aq NaHCO3 soln and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulphate anhydrous, filtered and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate) to give N-(1-dimethoxymethyl-cyclobutyl)-2-(3-ethynyl-quinolin-6-yloxy)-2methylsulfanyl-acetamide as white solid. 1H NMR (CDCl3) δ ppm: 8.84 (1H, d); 8.19 (1H, d); 8.05 (1H, d); 7.46 (1H, dd); 7.23 (1H, d); 6.86 (1H, br s); 5.62 (1H, s); 4.57 (1H, s); 3.51 (3H, s); 3.47 (3H, s); 3.28 (1H, s); 2.47-2.21 (4H, m); 2.21 (3H, 5); 2.01-1.73 (2H, m).

후처리

  1. additionwas added
  2. temperatureafter cooling to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulphate anhydrous
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-31751f19c05347bb8ca4b2d0b8471d98
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415272B2

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