Lithium Hydroxide → 1-{[5-(1-methyl-1H-indol-2-yl)-pyridin-3-ylamino]-methyl}-cyclobutanecarboxylic acid

HRID 593664Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 593664
C([O:3][C:4]([C:6]1([CH2:10][NH:11][C:12]2[CH:13]=[N:14][CH:15]=[C:16]([C:18]3[N:19]([CH3:27])[C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:17]=2)[CH2:9][CH2:8][CH2:7]1)=[O:5])C.[OH-].[Li+]>C1COCC1.CO>[CH3:27][N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[C:18]1[C:16]1[CH:17]=[C:12]([NH:11][CH2:10][C:6]2([C:4]([OH:5])=[O:3])[CH2:9][CH2:8][CH2:7]2)[CH:13]=[N:14][CH:15]=1

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 595346291-{[5-(1-methyl-1H-indol-2-yl)-pyridin-3-ylamino]-methyl}-cyclobutanecarboxylic acid ethyl ester

Produkt 1

HCID 595346611-{[5-(1-methyl-1H-indol-2-yl)-pyridin-3-ylamino]-methyl}-cyclobutanecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-{[5-(1-methyl-1H-indol-2-yl)-pyridin-3-ylamino]-methyl}-cyclobutanecarboxylic acid ethyl ester (0.107 g, 0.288 mmol) in THF (2 mL) and methanol (1 mL) is added aqueous lithium hydroxide (1M, 0.58 mL, 0.58 mmol) and the solution is stirred overnight. The product is isolated by RP HPLC on an Xbridge C18 eluting with an acetonitrile in 0.1% aqueous NH4OH gradient to give 1-{[5-(1-methyl-1H-indol-2-yl)-pyridin-3-ylamino]-methyl}-cyclobutanecarboxylic acid as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.74-1.86 (m, 1H), 1.87-1.97 (m, 3H), 2.26-2.35 (m, 2H), 3.33 (br. s., 1H), 3.39 (s, 2H), 3.75 (s, 3H), 6.60 (s, 1H), 7.05-7.09 (m, 1H), 7.15 (m, 1H), 7.17-7.21 (m, 1H), 7.50 (d, J=8.3 Hz, 1H), 7.57 (d, J=7.7 Hz, 1H), 7.94 (d, J=1.8 Hz, 1H), 8.06 (d, J=2.7 Hz, 1H). MS (ESI) m/z 336 (M+H)+.

Aufarbeitung

  1. customThe product is isolated by RP HPLC on an Xbridge
  2. washC18 eluting with an acetonitrile in 0.1% aqueous NH4OH gradient

Quellen und Nachweise

ORD-Eintrag
ord-15ca178d734a4667bfee949f2e5d4b08
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242963B2

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