Diisopropylethylamine → 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide

HRID 1799119

반응식

HRID 1799119 반응식
C[NH3+].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.[O:34]1[CH2:38][CH2:37][O:36][CH:35]1[CH2:39][CH2:40][C:41]1[S:45][C:44]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[N:43][C:42]=1[C:52]([OH:54])=O.CCN(C(C)C)C(C)C.[N:64]1[C:72]2[C:67](=[N:68][CH:69]=[CH:70][CH:71]=2)[S:66][C:65]=1[C:73]1[CH:79]=[CH:78][CH:77]=[CH:76][C:74]=1[NH2:75].C([O-])(O)=O.[Na+]>CN(C=O)C>[O:36]1[CH2:37][CH2:38][O:34][CH:35]1[CH2:39][CH2:40][C:41]1[S:45][C:44]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)=[N:43][C:42]=1[C:52]([NH:75][C:74]1[CH:76]=[CH:77][CH:78]=[CH:79][C:73]=1[C:65]1[S:66][C:67]2[C:72]([N:64]=1)=[CH:71][CH:70]=[CH:69][N:68]=2)=[O:54]

참가 물질

7

반응물 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 581014682-(Thiazolo[5,4-b]pyridin-2-yl)anilineHCID 585519085-(2-(1,3-Dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylic acidHCID 866211442-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium

생성물 1

HCID 585519015-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide수율 66%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (HATU) (669 mg, 1.8 mmol) was added to a solution of 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylic acid (504 mg, 1.7 mmol), DIPEA (613 μL, 3.5 mmol), and 2-(thiazolo[5,4-b]pyridin-2-yl)aniline b(250 mg, 1.1 mmol) in DMF (7 mL). The reaction mixture was stirred for 16 h, poured into sat aq NaHCO3 and extracted with EtOAc. The organic fractions were washed with brine, dried and concentrated. The crude product was crystallized from EtOH to give 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide (372 mg, 66% yield).

후처리

  1. additionpoured
  2. extractionextracted with EtOAc
  3. washThe organic fractions were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was crystallized from EtOH

출처 및 근거

ORD 기록
ord-daf8f2ab3a134fd9b0af9d92f9cc8dce
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343997B2

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