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6-Methylpyridine-2-carboxylic acid → N-(6-{6-Chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}-1H-indazol-4-yl)-6-methyl-2-pyridinecarboxamide

HRID 1695794
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1695794
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.ClC(N(C)C)=C(C)C.[NH2:19][C:20]1[CH:28]=[C:27]([C:29]2[CH:30]=[C:31]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[C:32]([Cl:35])=[N:33][CH:34]=2)[CH:26]=[C:25]2[C:21]=1[CH:22]=[N:23][N:24]2S(C1C=CC=CC=1)(=O)=O>C(Cl)Cl>[Cl:35][C:32]1[N:33]=[CH:34][C:29]([C:27]2[CH:26]=[C:25]3[C:21]([CH:22]=[N:23][NH:24]3)=[C:20]([NH:19][C:8]([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=3)=[O:10])[CH:28]=2)=[CH:30][C:31]=1[NH:36][S:37]([CH3:40])(=[O:39])=[O:38]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 702826-Methylpyridine-2-carboxylic acidHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 58255829N-{5-[4-Amino-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-chloro-3-pyridinyl}methanesulfonamide

Produkt 1

HCID 44539827N-(6-{6-Chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}-1H-indazol-4-yl)-6-methyl-2-pyridinecarboxamideAusbeute 41,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

6-Methyl-2-pyridinecarboxylic acid (43 mg) was dissolved in DCM (2 ml) and 1-chloro-N,N,2-trimethyl-1-propen-1-amine (0.042 ml) was added. The reaction was stirred for 15 mins. N-{5-[4-Amino-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-chloro-3-pyridinyl}methane sulfonamide (100 mg) in DCM (4 ml) was added and the reaction left at RT. The reaction was evaporated to dryness. IPA (3 ml) was added to the residue followed by 2M NaOH (aq) (3 ml) and the reaction was left overnight. The solution was neutralised using 2M HCl (aq) and then concentrated. The precipitate that formed was filtered then DMSO was added to the precipitate. Attempts to filter the solid failed so the reaction was blown down under a stream of nitrogen. The residue was redissolved in DMSO (0.5 ml) and purified by MDAP (method E). The pure fraction was evaporated to dryness to give title compound (40 mg).

Aufarbeitung

  1. waitthe reaction left at RT
  2. customThe reaction was evaporated to dryness
  3. additionIPA (3 ml) was added to the residue
  4. waitthe reaction was left overnight
  5. concentrationconcentrated
  6. customThe precipitate that formed
  7. filtrationwas filtered
  8. additionDMSO was added to the precipitate
  9. filtrationto filter the solid
  10. dissolutionThe residue was redissolved in DMSO (0.5 ml)
  11. custompurified by MDAP (method E)
  12. customThe pure fraction was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-af5b9c87623e461fb419fcc5f79ac653
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08163743B2

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