1-Hydroxybenzotriazole → (4-{4-[5-(6-Benzyloxy-naphthalen-2-yl)-pyrazolo[1,5-c]pyrimidin-7-ylamino]-phenylcarbamoyl}-benzyl)-carbamic acid tert-butyl ester

HRID 19601

Reaktionsgleichung

Reaktionsgleichung von HRID 19601
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH2:41]([O:48][C:49]1[CH:50]=[C:51]2[C:56](=[CH:57][CH:58]=1)[CH:55]=[C:54]([C:59]1[N:64]=[C:63]([NH:65][C:66]3[CH:71]=[CH:70][C:69]([NH2:72])=[CH:68][CH:67]=3)[N:62]3[N:73]=[CH:74][CH:75]=[C:61]3[CH:60]=1)[CH:53]=[CH:52]2)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CN(C=O)C.C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14](=[O:16])[NH:72][C:69]2[CH:70]=[CH:71][C:66]([NH:65][C:63]3[N:62]4[N:73]=[CH:74][CH:75]=[C:61]4[CH:60]=[C:59]([C:54]4[CH:53]=[CH:52][C:51]5[C:56](=[CH:57][CH:58]=[C:49]([O:48][CH2:41][C:42]6[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=6)[CH:50]=5)[CH:55]=4)[N:64]=3)=[CH:67][CH:68]=2)=[CH:17][CH:18]=1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 8536054-(((tert-Butoxycarbonyl)amino)methyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67318736N-[5-(6-benzyloxy-naphthalen-2-yl)-pyrazolo[1,5-c]pyrimidin-7-yl]-benzene-1,4-diamine2×

Produkt 1

HCID 67319336(4-{4-[5-(6-Benzyloxy-naphthalen-2-yl)-pyrazolo[1,5-c]pyrimidin-7-ylamino]-phenylcarbamoyl}-benzyl)-carbamic acid tert-butyl esterAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 4-(tert-butoxycarbonylamino-methyl)-benzoic acid (251 mg) and N-hydroxy-benzotriazole (HOBt)(153 mg) in DMF (10 ml) are added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC)(575 mg) and triethylamine (0.416 ml). The mixture is stirred for 0.5 h at ambient temperature. To this solution is added N-[5-(6-benzyloxy-naphthalen-2-yl)-pyrazolo[1,5-c]pyrimidin-7-yl]-benzene-1,4-diamine (compound B2)(0.38 g). After completion of the reaction the mixture is evaporated at high vacuum and the residue is treated with methanol. The resulting solid is filtered and dried. A colorless solid (0.523 g) is obtained in 91% yield.

Aufarbeitung

  1. customAfter completion of the reaction the mixture
  2. customis evaporated at high vacuum
  3. additionthe residue is treated with methanol
  4. filtrationThe resulting solid is filtered
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a886560291e048058a8715903015ab00
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745446B2

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