Hydrochloric Acid → N-{3-[5-{2-[(2-Aminoethyl)amino]-4-pyrimidinyl}-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide

HRID 590203Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 590203
Cl.O1CCOCC1.CC([N:12]([CH2:16][CH2:17][NH:18][C:19]1[N:24]=[C:23]([C:25]2[S:29][C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])=[N:27][C:26]=2[C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([NH:40][S:41]([C:44]3[CH:49]=[C:48]([F:50])[CH:47]=[CH:46][C:45]=3[F:51])(=[O:43])=[O:42])[C:35]=2[F:52])[CH:22]=[CH:21][N:20]=1)C(=O)[O-])(C)C.CO>C(Cl)Cl>[NH2:12][CH2:16][CH2:17][NH:18][C:19]1[N:24]=[C:23]([C:25]2[S:29][C:28]([C:30]([CH3:33])([CH3:31])[CH3:32])=[N:27][C:26]=2[C:34]2[C:35]([F:52])=[C:36]([NH:40][S:41]([C:44]3[CH:49]=[C:48]([F:50])[CH:47]=[CH:46][C:45]=3[F:51])(=[O:42])=[O:43])[CH:37]=[CH:38][CH:39]=2)[CH:22]=[CH:21][N:20]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 312751,4-DioxaneHCID 867130171,1-Dimethylethyl[2-({4-[4-(3-{[(2,5-difluorophenyl)sulfonyl]amino}-2-fluorophenyl)-2-(1,1-dimethylethyl)-1,3-thiazol-5-yl]-2-pyrimidinyl}amino)ethyl]carbamate

Produkt 1

HCID 57989685N-{3-[5-{2-[(2-Aminoethyl)amino]-4-pyrimidinyl}-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamideAusbeute 117,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 4N solution of HCl in 1,4-dioxane (1.7 ml, 7.1 mmol) was added to a stirring solution of 1,1-dimethylethyl[2-({4-[4-(3-{[(2,5-difluorophenyl)sulfonyl]amino}-2-fluorophenyl)-2-(1,1-dimethylethyl)-1,3-thiazol-5-yl]-2-pyrimidinyl}amino)ethyl]carbamate (0.31 g, 0.47 mmol) (composite batches prepared as described in the previous step) in DCM (10 ml) at rt. MeOH (1 ml) was added to aid in solubility. The reaction was allowed to stir at rt for 3 h. The volatiles were removed and the residue was dried in vacuo to afford the title compound of Step B (0.31 g, quantitative yield) as a hydrochloride salt that was used without further purification; 1H NMR (400 MHz, DMSO-d6) δ ppm 10.77 (s, 1H), 7.93-8.18 (m, 4H), 7.20-7.69 (m, 7H), 3.37-3.53 (m, 2H), 2.96 (d, J=5.1 Hz, 2H), 1.41 (s, 9H). MS (ES+): 563 [M+H]+.

Aufarbeitung

  1. customprepared
  2. customat rt
  3. customThe volatiles were removed
  4. customthe residue was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-00c01928e1d645d187abf07f5c10daf3
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233956B2

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