(R)-2-(2-(2,4-Dimethoxybenzyl)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-N,4-dimethylpentanamide → (R)-2-(7-Fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-N,4-dimethylpentanamide

HRID 2092871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2092871
COC1C=C(OC)C=CC=1C[N:6]1[CH2:14][C:13]2[C:12]([F:15])=[C:11]([NH:16][C@H:17]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:18]([NH:20][CH3:21])=[O:19])[N:10]=[C:9]([C:26]3[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=3)[C:8]=2[C:7]1=[O:32]>C(O)(C(F)(F)F)=O>[F:15][C:12]1[C:13]2[CH2:14][NH:6][C:7](=[O:32])[C:8]=2[C:9]([C:26]2[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=2)=[N:10][C:11]=1[NH:16][C@H:17]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:18]([NH:20][CH3:21])=[O:19]

Komponenten

3

Edukt 1

HCID 67238387(R)-2-(2-(2,4-Dimethoxybenzyl)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-N,4-dimethylpentanamide

Produkt 1

HCID 53251341(R)-2-(7-Fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-N,4-dimethylpentanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of (R)-2-(2-(2,4-dimethoxybenzyl)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-N,4-dimethylpentanamide (38 mg, 0.072 mmol) in TFA (5 mL) was heated to 65° C. for 4 h. After removal of the solvent, the residue was diluted in MeOH (2 mL) and was purified by preparative HPLC eluting with water (0.05% TFA) and ACN (25-30%, gradient, 0.035% TFA). The collected fractions were stripped to dryness to give the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 0.84-0.93 (m, 6H), 1.63-1.81 (m, 2H), 2.57 (d, J=4.39 Hz, 3H), 3.88 (s, 3H), 4.04-4.19 (m, 2H), 4.36 (s, 2H), 6.99 (d, J=7.32 Hz, 1H), 7.61-7.76 (m, 1H), 7.93 (d, J=4.39 Hz, 1H), 8.30 (s, 1H), 8.83 (s, 1H). [M+H] calc'd for C18H23FN6O2, 375. found, 375.

Aufarbeitung

  1. customAfter removal of the solvent
  2. additionthe residue was diluted in MeOH (2 mL)
  3. customwas purified by preparative HPLC
  4. washeluting with water (0.05% TFA) and ACN (25-30%, gradient, 0.035% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-f66f3bd548164a018a26c93ebbbc9aab
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440689B2

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