1-Hydroxybenzotriazole → [2-(4-{4-[5-(4'-Fluoro-biphenyl-4-yl)-pyrazolo[1,5-c]pyrimidin-7-ylamino]-phenylcarbamoyl}-phenyl)-ethyl]-carbamic acid tert-butyl ester

HRID 19605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 19605
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[F:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][C:52]([C:55]3[N:60]=[C:59]([NH:61][C:62]4[CH:67]=[CH:66][C:65]([NH2:68])=[CH:64][CH:63]=4)[N:58]4[N:69]=[CH:70][CH:71]=[C:57]4[CH:56]=3)=[CH:51][CH:50]=2)=[CH:45][CH:44]=1>CN(C=O)C.C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:15](=[O:17])[NH:68][C:65]2[CH:66]=[CH:67][C:62]([NH:61][C:59]3[N:58]4[N:69]=[CH:70][CH:71]=[C:57]4[CH:56]=[C:55]([C:52]4[CH:53]=[CH:54][C:49]([C:46]5[CH:47]=[CH:48][C:43]([F:42])=[CH:44][CH:45]=5)=[CH:50][CH:51]=4)[N:60]=3)=[CH:63][CH:64]=2)=[CH:18][CH:19]=1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 166409054-(2-{[(Tert-butoxy)carbonyl]amino}ethyl)benzoic acidHCID 67319451N-[5-(4'-Fluoro-biphenyl-4-yl)-pyrazolo[1,5-c]pyrimidin-7-yl]-benzene-1,4-diamine2×

Produkt 1

HCID 67318621[2-(4-{4-[5-(4'-Fluoro-biphenyl-4-yl)-pyrazolo[1,5-c]pyrimidin-7-ylamino]-phenylcarbamoyl}-phenyl)-ethyl]-carbamic acid tert-butyl esterAusbeute 59,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 4-(tert-butoxycarbonylamino-ethyl)-benzoic acid (78 mg) and N-hydroxy-benzotriazole (HOBt)(45 mg) in DMF (5 ml) are added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC)(150 mg) and triethylamine (0.27 ml). The mixture is stirred for 0.5 h at ambient temperature. To this solution is added N-[5-(4′-Fluoro-biphenyl-4-yl)-pyrazolo[1,5-c]pyrimidin-7-yl]-benzene-1,4-diamine (compound B4)(0.1 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 yellow solid (0.097 g) is obtained.

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-aa35adbbc8be40a9bd00900762ae80f9
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745446B2

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