1,2-Dichloroethane → 1,1-dimethylethyl (2S)-4-[(5'-{[({2-chloro-5-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)sulfonyl]-4-fluorophenyl}carbonyl)amino]methyl}-2'-fluoro-3-biphenylyl)methyl]-2-methyl-1-piperazinecarboxylate

HRID 564647Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 564647
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([S:12]([NH:15][CH2:16][C:17]2[C:18]([NH:30][CH:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[C:19]3[CH:27]=[N:26][N:25]([CH2:28][CH3:29])[C:20]3=[N:21][C:22]=2[CH2:23][CH3:24])(=[O:14])=[O:13])=[CH:7][C:3]=1[C:4](O)=[O:5].[NH2:37][CH2:38][C:39]1[CH:40]=[CH:41][C:42]([F:66])=[C:43]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([CH2:51][N:52]3[CH2:57][CH2:56][N:55]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[C@@H:54]([CH3:65])[CH2:53]3)[CH:46]=2)[CH:44]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([S:12]([NH:15][CH2:16][C:17]2[C:18]([NH:30][CH:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)=[C:19]3[CH:27]=[N:26][N:25]([CH2:28][CH3:29])[C:20]3=[N:21][C:22]=2[CH2:23][CH3:24])(=[O:13])=[O:14])=[CH:7][C:3]=1[C:4]([NH:37][CH2:38][C:39]1[CH:40]=[CH:41][C:42]([F:66])=[C:43]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([CH2:51][N:52]3[CH2:57][CH2:56][N:55]([C:58]([O:60][C:61]([CH3:62])([CH3:64])[CH3:63])=[O:59])[C@@H:54]([CH3:65])[CH2:53]3)[CH:46]=2)[CH:44]=1)=[O:5]

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 251325161,1-dimethylethyl (2S)-4-{[5'-(aminomethyl)-2'-fluoro-3-biphenylyl]methyl}-2-methyl-1-piperazinecarboxylateHCID 578132602-chloro-5-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)sulfonyl]-4-fluorobenzoic acid

Produkt 1

HCID 866332011,1-dimethylethyl (2S)-4-[(5'-{[({2-chloro-5-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)sulfonyl]-4-fluorophenyl}carbonyl)amino]methyl}-2'-fluoro-3-biphenylyl)methyl]-2-methyl-1-piperazinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

345(b) The 2-chloro-5-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)sulfonyl]-4-fluorobenzoic acid, was dissolved in 3 mL of DCM with 1,1-dimethylethyl (2S)-4-{[5′-(aminomethyl)-2′-fluoro-3-biphenylyl]methyl}-2-methyl-1-piperazinecarboxylate (41.3 mg, 0.1 mmol), and then added in HOBt (1.0 eq, 14.0 mg), and EDC (1.0 eq, 19.0 mg). The resultant solution was stirred overnight. The solution was then purified using a Gilson to give 1,1-dimethylethyl (2S)-4-[(5′-{[({2-chloro-5-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)sulfonyl]-4-fluorophenyl}carbonyl)amino]methyl}-2′-fluoro-3-biphenylyl)methyl]-2-methyl-1-piperazinecarboxylate.

Aufarbeitung

  1. customThe solution was then purified

Quellen und Nachweise

ORD-Eintrag
ord-f09bc4039ca94aa99d81e81ba9be0523
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067408B2

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