4-amino-N-methylbenzene-1-sulfonamide → 4-(6-chloro-4-pyrrolidin-1-yl-pyridin-2-ylamino)-N-methyl-benzenesulfonamide

HRID 1437749노트

반응식

HRID 1437749 반응식
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([Cl:13])[N:3]=1.CC(C)([O-])C.[K+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[NH2:66][C:67]1[CH:72]=[CH:71][C:70]([S:73]([NH:76][CH3:77])(=[O:75])=[O:74])=[CH:69][CH:68]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:13][C:4]1[N:3]=[C:2]([NH:66][C:67]2[CH:72]=[CH:71][C:70]([S:73]([NH:76][CH3:77])(=[O:75])=[O:74])=[CH:69][CH:68]=2)[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=1

참가 물질

8

반응물 4

HCID 743684-amino-N-methylbenzene-1-sulfonamideHCID 634876Binap, (A+-)-HCID 11644208HCID 11644208, 화합물HCID 23665647Potassium tert-butoxide

생성물 1

HCID 116392174-(6-chloro-4-pyrrolidin-1-yl-pyridin-2-ylamino)-N-methyl-benzenesulfonamide수율 24.6%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

To a solution of 2,6-dichloro-4-pyrrolidino-pyridine (0.350 g, 1.62 mmol) in toluene (6 mL) were added potassium tert-butoxide (0.132 g, 1.18 mmol), palladium(II)-acetate (36.40 mg, 0.160 mmol), BINAP (32 mg, 0.514 mmol) and 4-amino-N-methyl-benzenesulfonamide (227 mg, 1.22 mmol) in a 10 mL reaction vessel. This reaction mixture was subjected the microwave irradiation, in which the microwave power was 250 W, to attain a reaction temperature of 150° C. After this reaction proceeded for 30 min, water (150 mL) was added to the reaction mixture and the reaction product was extracted with ethyl acetate. The organic layer was dried over sodium sulphate, filtered, and the filtrate concentrated under vacuum. The product was purified through column chromatography using 230-400 mesh silica gel (elution 20:80 acetone:petroleum ether) to afford the desired compound as a light brown solid (110 mg, yield 19%).

후처리

  1. customin a 10 mL reaction vessel
  2. customthe microwave irradiation
  3. customa reaction temperature of 150° C
  4. extractionthe reaction product was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe product was purified through column chromatography

출처 및 근거

ORD 기록
ord-c614b00504ad44569f7b6db84973d737
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622486B2

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