N-(4-aminocyclohexyl)methanesulfonamide → HCID 178505151, Verbindung

HRID 1670971

Reaktionsgleichung

Reaktionsgleichung von HRID 1670971
Cl[C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[N:10][C:9]=2[C:18]2[CH:19]=[C:20]([NH:24][S:25]([C:28]3[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:29]=3[F:35])(=[O:27])=[O:26])[CH:21]=[CH:22][CH:23]=2)[CH:5]=[CH:4][N:3]=1.[NH2:36][CH:37]1[CH2:42][CH2:41][CH:40]([NH:43][S:44]([CH3:47])(=[O:46])=[O:45])[CH2:39][CH2:38]1>C(O)CCC>[F:35][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([F:34])[C:28]=1[S:25]([NH:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:9]2[N:10]=[C:11]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[S:12][C:8]=2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:36][C@H:37]3[CH2:42][CH2:41][C@H:40]([NH:43][S:44]([CH3:47])(=[O:46])=[O:45])[CH2:39][CH2:38]3)[N:7]=2)[CH:19]=1)(=[O:27])=[O:26]

Komponenten

4

Edukt 2

HCID 18348422N-(4-aminocyclohexyl)methanesulfonamideHCID 57989807N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1-pyrrolidinyl)-1,3-thiazol-4-yl]phenyl}-2,6-difluorobenzenesulfonamide

Produkt 1

HCID 178505151HCID 178505151, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1-pyrrolidinyl)-1,3-thiazol-4-yl]phenyl}-2,6-difluorobenzenesulfonamide was dissolved in n-butanol and N-(4-aminocyclohexyl)methanesulfonamide (27.0 mg, 0.140 mmol) was added at rt followed by TEA (52.2 μl, 0.375 mmol). The reaction was heated to 60° C. for 12 h. Purified via Gilson Acidic HPLC (10 to 90% gradient, Acetonitrile/H2O+TFA; C18 column). Desired fractions were combined and washed with NaHCO3, dried over MgSO4 and solvent removed to give the title compound as a yellow solid (0.010 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.73 (d, J=5.1 Hz, 1H), 7.38-7.55 (m, 1H), 7.11-7.31 (m, 2H), 6.93-7.10 (m, 3H), 6.72-6.88 (m, 1H), 6.42-6.48 (m, 1H), 6.28-6.35 (m, 1H), 5.79-5.88 (m, 1H), 3.52-3.63 (m, 1H), 3.29-3.45 (m, 6H), 3.05-3.16 (m, 1H), 2.91 (s, 3H), 1.77-2.02 (m, 6H), 1.19-1.42 (m, 4H). MS (ESI): 690 [M+H]+.

Aufarbeitung

  1. customPurified via Gilson Acidic HPLC (10 to 90% gradient, Acetonitrile/H2O+TFA; C18 column)
  2. washwashed with NaHCO3
  3. dry with materialdried over MgSO4 and solvent
  4. customremoved

Quellen und Nachweise

ORD-Eintrag
ord-015337227c324a9e9901b93265f27154
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07994185B2

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