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4-Methylmorpholine → tert-Butyl (2-{4-[({2-[(2,3-difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}amino)sulfonyl]piperazin-1-yl}-2-oxoethyl)carbamate

HRID 2388888
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2388888
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.ON1C2C=CC=CC=2N=N1.Cl.N1(S(N)(=O)=O)CCNCC1.Cl.[F:36][C:37]1[C:42]([F:43])=[CH:41][CH:40]=[CH:39][C:38]=1[CH2:44][S:45][C:46]1[N:51]=[C:50]([NH:52][S:53]([N:56]2[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]2)(=[O:55])=[O:54])[CH:49]=[C:48]([O:62][CH3:63])[N:47]=1.CN1CCOCC1>CN(C=O)C>[F:36][C:37]1[C:42]([F:43])=[CH:41][CH:40]=[CH:39][C:38]=1[CH2:44][S:45][C:46]1[N:51]=[C:50]([NH:52][S:53]([N:56]2[CH2:57][CH2:58][N:59]([C:10](=[O:12])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:60][CH2:61]2)(=[O:54])=[O:55])[CH:49]=[C:48]([O:62][CH3:63])[N:47]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27960291-Hydroxybenzotriazole hydrateHCID 67467256Piperazine-1-sulfonamide hydrochlorideHCID 131728548N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-methoxypyrimidin-4-yl]piperazine-1-sulfonamide, hydrochloride salt

Produkt 1

HCID 86619892
tert-Butyl (2-{4-[({2-[(2,3-difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}amino)sulfonyl]piperazin-1-yl}-2-oxoethyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of N-(tert-butoxycarbonyl)glycine (0.11 g) in DMF (10 mL) was added 1,3-Dicyclohexycarbodiimide (0.14 g) and 1-hydroxybenzotriazole hydrate (94 mg). After stirring at room temperature for 1 h, a solution of N42-[[(2,3-Difluorophenyl)methyl]thio]-6-methoxypyrimidin-4-yl]piperazine-1-sulfonamide, hydrochloride salt (the product of step i, 0.27 g) and N-methylmorpholine (78 μL) in DMF (5 mL) was added dropwise and stirring continued at room temperature for 24 h. The mixture was filtered, rinsed with DCM and the filtrate evaporated. The crude material was purified by column chromatography on silica gel using EtOAc/isohexane (3:2) as eluent to give the subtitle compound as a foam. Yield: 0.24 g

Aufarbeitung

  1. stirringstirring
  2. waitcontinued at room temperature for 24 h
  3. filtrationThe mixture was filtered
  4. washrinsed with DCM
  5. customthe filtrate evaporated
  6. customThe crude material was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-33a618244bbe4fda89050bf0aeddc24b
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08269002B2

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