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

HRID 590207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 590207
Cl.O1CCOCC1.[Cl:8][C:9]1[N:14]=[C:13]([C:15]2[S:19][C:18]([N:20]3[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]3)=[N:17][C:16]=2[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([NH:39][S:40]([C:43]3[CH:48]=[C:47]([F:49])[CH:46]=[CH:45][C:44]=3[F:50])(=[O:42])=[O:41])[C:34]=2[F:51])[CH:12]=[CH:11][N:10]=1>C(Cl)Cl.CO>[Cl:8][C:9]1[N:14]=[C:13]([C:15]2[S:19][C:18]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)=[N:17][C:16]=2[C:33]2[C:34]([F:51])=[C:35]([NH:39][S:40]([C:43]3[CH:48]=[C:47]([F:49])[CH:46]=[CH:45][C:44]=3[F:50])(=[O:42])=[O:41])[CH:36]=[CH:37][CH:38]=2)[CH:12]=[CH:11][N:10]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 579899561,1-Dimethylethyl 4-[5-(2-chloro-4-pyrimidinyl)-4-(3-{[(2,5-difluorophenyl)sulfonyl]amino}-2-fluorophenyl)-1,3-thiazol-2-yl]-1-piperazinecarboxylate

Produkt 1

HCID 57989746N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1-piperazinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamideAusbeute 130,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 4N solution of HCl in 1,4-dioxane (1.1 ml, 4.3 mmol) was added to a stirring solution of 1,1-dimethylethyl 4-[5-(2-chloro-4-pyrimidinyl)-4-(3-{[(2,5-difluorophenyl)sulfonyl]amino}-2-fluorophenyl)-1,3-thiazol-2-yl]-1-piperazinecarboxylate (0.36 g, 0.54 mmol) in DCM (8 mL) and MeOH (1 mL) at rt. The reaction was allowed to stir overnight. LCMS analysis indicated complete consumption of the starting material. The volatiles were removed in vaccuo to afford the HCl salt of the desired product of Step C (0.40 g, 100% yield) which was carried forward without further purification. MS (ES+): 568 [M+H]+.

Aufarbeitung

  1. customconsumption of the starting material
  2. customThe volatiles were removed in vaccuo

Quellen und Nachweise

ORD-Eintrag
ord-5b99c3adec1349db95799bd08efdf5b6
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233956B2

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