Sulfoxonium, trimethyl-, iodide (1:1) → ethyl 2-[4-amino-3-(3-methoxy-4-{[(1-methyl-1H-indol-2-yl)carbonyl]amino}phenyl)thieno[3,2-c]pyridin-7-yl]cyclopropanecarboxylate

HRID 17241

반응식

HRID 17241 반응식
[I-].[CH3:2][S+](C)(C)=O.[NH2:7][C:8]1[C:13]2[C:14]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24]([C:26]4[N:27]([CH3:35])[C:28]5[C:33]([CH:34]=4)=[CH:32][CH:31]=[CH:30][CH:29]=5)=[O:25])=[C:19]([O:36][CH3:37])[CH:18]=3)=[CH:15][S:16][C:12]=2[C:11](/[CH:38]=[CH:39]/[C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:10][N:9]=1>CS(C)=O.[H-].[Na+]>[NH2:7][C:8]1[C:13]2[C:14]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24]([C:26]4[N:27]([CH3:35])[C:28]5[C:33]([CH:34]=4)=[CH:32][CH:31]=[CH:30][CH:29]=5)=[O:25])=[C:19]([O:36][CH3:37])[CH:18]=3)=[CH:15][S:16][C:12]=2[C:11]([CH:38]2[CH2:2][CH:39]2[C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:10][N:9]=1

참가 물질

5

반응물 2

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 86596701ethyl (2E)-3-[4-amino-3-(3-methoxy-4-{[(1-methyl-1H-indol-2-yl)carbonyl]amino}phenyl)thieno[3,2-c]pyridin-7-yl]acrylate

생성물 1

HCID 18450882ethyl 2-[4-amino-3-(3-methoxy-4-{[(1-methyl-1H-indol-2-yl)carbonyl]amino}phenyl)thieno[3,2-c]pyridin-7-yl]cyclopropanecarboxylate수율 30.2%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 24758Sodium hydride용매

실험 절차

Trimethylsulfoxonium iodide (45.1 mg, 0.205 mmol) in anhydrous methyl sulfoxide (4 mL) and 60% sodium hydride in mineral oil (16.4 mg, 0.411 mmol) was stirred for 5 minutes at room temperature and treated with a mixture of ethyl (2E)-3-[4-amino-3-(3-methoxy-4-{[(1-methyl-1H-indol-2-yl)carbonyl]amino}phenyl)thieno[3,2-c]pyridin-7-yl]acrylate (108 mg, 0.205 mmol) in methyl sulfoxide (2 mL) was added. After 4 hours the mixture was cooled to room temperature and quenched with saturated ammonium chloride solution (7 mL). The aqueous layer was extracted with dichloromethane (3×10 mL), dried over magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The crude product was purified via HPLC preparative to give the title compound as a white solid (33.6 mg 0.062 mmol): LCMS (Conditions a): MH+=541 Rt =4.20 minutes; 1H NMR (DMSO-d6, 400 MHz) δ 9.51 (1 H), 7.99 (1 H), 7.69 (2 H), 7.58 (2 H), 7.35 (2 H), 7.18 (1 H), 7.15 (1 H), 7.06 (1 H), 5.49 (1 H), 4.18 (2 H), 4.04 (3 H), 3.91 (3 H), 2.45 (1 H), 1.86 (1 H), 1.56 (1 H), 1.47 (1 H), 1.26 (3 H).

후처리

  1. additionwas added
  2. customquenched with saturated ammonium chloride solution (7 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane (3×10 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe crude product was purified via HPLC preparative

출처 및 근거

ORD 기록
ord-518a35c6118b444aac791f8384dc4f0d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737160B2

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