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Diisopropylethylamine → tert-butyl 3-phenyl-5-(3-(pyridin-4-yl)-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate

HRID 1467327
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1467327
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[N:25]1[CH:30]=[CH:29][C:28]([C:31]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37]([C:40](O)=[O:41])[CH:38]=3)[N:33]([C:43]([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[N:32]=2)=[CH:27][CH:26]=1.[NH2:62][CH:63]1[CH2:68][CH:67]([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[CH2:66][N:65]([C:75]([O:77][C:78]([CH3:81])([CH3:80])[CH3:79])=[O:76])[CH2:64]1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:69]1([CH:67]2[CH2:68][CH:63]([NH:62][C:40]([C:37]3[CH:38]=[C:39]4[C:34](=[CH:35][CH:36]=3)[N:33]([C:43]([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)[N:32]=[C:31]4[C:28]3[CH:27]=[CH:26][N:25]=[CH:30][CH:29]=3)=[O:41])[CH2:64][N:65]([C:75]([O:77][C:78]([CH3:81])([CH3:80])[CH3:79])=[O:76])[CH2:66]2)[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1
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Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58592957Tert-butyl 3-amino-5-phenylpiperidine-1-carboxylateHCID 679963353-pyridin-4-yl-1-trityl-1H-indazole-5-carboxylic acid

Produkt 1

HCID 67995717
tert-butyl 3-phenyl-5-(3-(pyridin-4-yl)-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) (44 mg, 0.114 mmol) was added to a suspension of 3-(pyridin-4-yl)-1-trityl-1H-indazole-5-carboxylic acid (50 mg, 0.104 mmol) in DMF (0.5 mL) and was stirred at room temperature for 15 minutes. A solution of tert-butyl 3-amino-5-phenyl-piperidine-1-carboxylate (29 mg, 0.104 mmol) in DMF (0.5 mL) was added to the reaction and followed by diisopropyl ethyl amine (DIEA) (0.1 mL). The mixture was stirred at room temperature for an additional 30 minutes. The reaction was quenched with water (5 mL) and extracted with ethyl acetate (3×10 mL). The extracts were combined, dried using anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was progressed to the next step without purification.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for an additional 30 minutes
  2. customThe reaction was quenched with water (5 mL)
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was progressed to the next step without purification

Quellen und Nachweise

ORD-Eintrag
ord-b619998e938347f6a608b03093b2495c
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08999957B2

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