Dichloromethane → N-(3-{5-(2-Amino-4-pyrimidinyl)-2-[4-(methylsulfonyl)-1-piperazinyl]-1,3-thiazol-4-yl}-2-fluorophenyl)-2,5-difluorobenzenesulfonamide

HRID 1671107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1671107
Cl[C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([N:13]3[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]3)=[N:10][C:9]=2[C:23]2[C:24]([F:41])=[C:25]([NH:29][S:30]([C:33]3[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=3[F:40])(=[O:32])=[O:31])[CH:26]=[CH:27][CH:28]=2)[CH:5]=[CH:4][N:3]=1.[NH4+:42].[OH-].C(Cl)Cl>CO>[NH2:42][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([N:13]3[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]3)=[N:10][C:9]=2[C:23]2[C:24]([F:41])=[C:25]([NH:29][S:30]([C:33]3[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=3[F:40])(=[O:32])=[O:31])[CH:26]=[CH:27][CH:28]=2)[CH:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 14923Ammonium HydroxideHCID 57989647N-(3-{5-(2-Chloro-4-pyrimidinyl)-2-[4-(methylsulfonyl)-1-piperazinyl]-1,3-thiazol-4-yl}-2-fluorophenyl)-2,5-difluorobenzenesulfonamide

Produkt 1

HCID 57989758N-(3-{5-(2-Amino-4-pyrimidinyl)-2-[4-(methylsulfonyl)-1-piperazinyl]-1,3-thiazol-4-yl}-2-fluorophenyl)-2,5-difluorobenzenesulfonamideAusbeute 101,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of N-(3-{5-(2-chloro-4-pyrimidinyl)-2-[4-(methylsulfonyl)-1-piperazinyl]-1,3-thiazol-4-yl}-2-fluorophenyl)-2,5-difluorobenzenesulfonamide (0.14 g, 0.22 mmol) in NH4OH (2.5 mL, 65 mmol) was sealed in a microwave vial and irradiated at 140° C. for 12 min. LCMS analysis indicates complete conversion to product. The reaction mixture was transferred to a round bottom flask with DCM and MeOH. A precipitate formed while attempting to remove the volatiles in vacuo and it was collected by vacuum filtration. The pale yellow solid was dried in vacuo to afford the title compound (0.14 g, 100% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.76 (br. s., 1H), 7.84 (d, J=5.3 Hz, 1H), 7.46-7.61 (m, 3H), 7.38-7.46 (m, 1H), 7.22-7.34 (m, 2H), 6.59 (br. s., 2H), 5.64 (d, J=5.1 Hz, 1H), 3.60 (br. s., 4H), 3.26 (br. s., 4H), 2.92 (s, 3H). MS (ES+): 626 [M+H]+.

Aufarbeitung

  1. customirradiated at 140° C. for 12 min
  2. customA precipitate formed
  3. customto remove the volatiles in vacuo and it
  4. filtrationwas collected by vacuum filtration
  5. customThe pale yellow solid was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1cc77ac1ad7246a4af4b150bc98277bd
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994185B2

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