Dimethylformamide → N-(4-(methoxymethyl)-5-(thiazolo[5,4-c]pyridin-2-yl)thiazol-2-yl)-N-((S)-2-(4-nitrophenylsulfonamido)-3-(4-(trifluoromethyl)phenyl)propyl)acetamide

HRID 661031노트

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HRID 661031 반응식
[CH3:1][O:2][CH2:3][C:4]1[N:5]=[C:6]([NH:18][C:19](=[O:21])[CH3:20])[S:7][C:8]=1[C:9]1[S:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][C:16]=2[N:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C.[F:33][C:34]([F:58])([F:57])[C:35]1[CH:56]=[CH:55][C:38]([CH2:39][CH:40]2[CH2:42][N@@:41]2[S:43]([C:46]2[CH:51]=[CH:50][C:49]([N+:52]([O-:54])=[O:53])=[CH:48][CH:47]=2)(=[O:45])=[O:44])=[CH:37][CH:36]=1>C(Cl)Cl.CO>[CH3:1][O:2][CH2:3][C:4]1[N:5]=[C:6]([N:18]([CH2:42][C@@H:40]([NH:41][S:43]([C:46]2[CH:47]=[CH:48][C:49]([N+:52]([O-:54])=[O:53])=[CH:50][CH:51]=2)(=[O:44])=[O:45])[CH2:39][C:38]2[CH:55]=[CH:56][C:35]([C:34]([F:57])([F:33])[F:58])=[CH:36][CH:37]=2)[C:19](=[O:21])[CH3:20])[S:7][C:8]=1[C:9]1[S:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][C:16]=2[N:17]=1

참가 물질

7

반응물 4

HCID 6228Dimethylformamide2회HCID 10796Cesium carbonateHCID 57633920N-(4-(methoxymethyl)-5-(thiazolo[5,4-c]pyridin-2-yl)thiazol-2-yl)acetamideHCID 178526727HCID 178526727, 화합물

생성물 1

HCID 57931099N-(4-(methoxymethyl)-5-(thiazolo[5,4-c]pyridin-2-yl)thiazol-2-yl)-N-((S)-2-(4-nitrophenylsulfonamido)-3-(4-(trifluoromethyl)phenyl)propyl)acetamide수율 43.8%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

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온도
50 °C

실험 절차

To a 50 mL round-bottomed flask was added N-(4-(methoxymethyl)-5-(thiazolo[5,4-c]pyridin-2-yl)thiazol-2-yl)acetamide (0.300 g, 0.936 mmol), Cs2CO3 (0.610 g, 1.87 mmol), and DMF (0.0721 mL, 0.936 mmol). The resulting solution was heated to 50° C. A DMF solution of (S)-2-(4-(trifluoromethyl)benzyl)-1-(4-nitrophenylsulfonyl)aziridine (0.724 g, 1.87 mmol) was added to the reaction dropwise, and the reaction mixture was monitored by LCMS. After approximately 30 minutes, the solvent was removed and the residue was taken up in EtOAc and washed with saturated sodium bicarbonate. The solution was dried over sodium sulfate, filtered and loaded onto a plug of silica gel. Chromatography through a Redi-Sep® pre-packed silica gel column (40 g), eluting with a gradient of 1% to 10% 2 M NH3.MeOH in DCM, to provide N-(4-(methoxymethyl)-5-(thiazolo[5,4-c]pyridin-2-yl)thiazol-2-yl)-N—((S)-2-(4-nitrophenylsulfonamido)-3-(4-(trifluoromethyl)phenyl)propyl)acetamide (0.290 g, 0.410 mmol, 43.8% yield). LCMS (M+H) 707 calc. for C29H26F3N6O6S3 707.1.

후처리

  1. customthe solvent was removed
  2. washwashed with saturated sodium bicarbonate
  3. dry with materialThe solution was dried over sodium sulfate
  4. filtrationfiltered
  5. washChromatography through a Redi-Sep® pre-packed silica gel column (40 g), eluting with a gradient of 1% to 10% 2 M NH3

출처 및 근거

ORD 기록
ord-52363da1bcd34161a8639a5cfcccd14e
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084479B2

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