1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl 3-((5-(3-(2-(tert-butyldimethylsilyloxy)ethylcarbamoyl)-1H-pyrrol-1-yl)-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

HRID 556829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 556829
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH:15][C:16]2[CH:21]=[C:20]([NH:22][C:23]3[CH:28]=[N:27][C:26]([C:29]#[N:30])=[CH:25][N:24]=3)[N:19]=[CH:18][C:17]=2[N:31]2[CH:35]=[CH:34][C:33]([C:36](O)=[O:37])=[CH:32]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Si:39]([O:46][CH2:47][CH2:48][NH2:49])([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40].C(N(C(C)C)C(C)C)C.O.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>CN(C=O)C>[Si:39]([O:46][CH2:47][CH2:48][NH:49][C:36]([C:33]1[CH:34]=[CH:35][N:31]([C:17]2[C:16]([NH:15][CH2:14][CH:10]3[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]3)=[CH:21][C:20]([NH:22][C:23]3[CH:28]=[N:27][C:26]([C:29]#[N:30])=[CH:25][N:24]=3)=[N:19][CH:18]=2)[CH:32]=1)=[O:37])([C:42]([CH3:44])([CH3:45])[CH3:43])([CH3:41])[CH3:40]

Komponenten

7

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 529218(2-Aminoethoxy)(tert-butyl)dimethylsilaneHCID 27960291-Hydroxybenzotriazole hydrateHCID 667465061-(4-((1-(tert-Butoxycarbonyl)piperidin-3-yl)methylamino)-6-(5-cyanopyrazin-2-ylamino)pyridin-3-yl)-1H-pyrrole-3-carboxylic acid

Produkt 1

HCID 66745676tert-butyl 3-((5-(3-(2-(tert-butyldimethylsilyloxy)ethylcarbamoyl)-1H-pyrrol-1-yl)-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-(4-((1-(tert-Butoxycarbonyl)piperidin-3-yl)methylamino)-6-(5-cyanopyrazin-2-ylamino)pyridin-3-yl)-1H-pyrrole-3-carboxylic acid (80 mg, 0.154 mmol) was dissolved in DMF (1.5 mL). 2-(tert-Butyldimethylsilyloxy)ethanamine (41 mg, 0.230 mmol), N-ethyldiisopropylamine (30 mg, 0.230 mmol), 1-hydroxy benzotriazole hydrate (31 mg, 0.230 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (44 mg, 0.23 mmol) were added to the solution and the reaction mixture was stirred for 14 h at room temperature. The solution was partitioned between dichloromethane and water. The two phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried (Na2SO4) and evaporated to give tert-butyl 3-((5-(3-(2-(tert-butyldimethylsilyloxy)ethylcarbamoyl)-1H-pyrrol-1-yl)-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (80 mg, 78%) which was used in the next step without purification.

Aufarbeitung

  1. customThe solution was partitioned between dichloromethane and water
  2. customThe two phases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-aac0b09ccfa546f38c5163156fd8069b
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058045B2

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