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 453305

反応式

HRID 453305 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d34b1801a0b94ee3a4538788698033ce
出典データセット
uspto-grants-2013_07
特許番号
US08492401B2

関連ノート

読み込み中…