Trifluoroacetic acid → Trifluoroacetic acid

HRID 516063Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516063
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]3[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]3[NH:23]C(=O)OC(C)(C)C)[N:10]=[C:9]([C:31]3[CH:32]=[N:33][N:34]([CH3:36])[CH:35]=3)[C:8]=2[C:7]1=[O:37].[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]>>[NH2:23][C@H:18]1[CH2:19][CH2:20][CH2:21][CH2:22][C@H:17]1[NH:16][C:11]1[N:10]=[C:9]([C:31]2[CH:32]=[N:33][N:34]([CH3:36])[CH:35]=2)[C:8]2[C:7](=[O:37])[NH:6][CH2:14][C:13]=2[C:12]=1[F:15].[C:44]([OH:50])([C:46]([F:49])([F:48])[F:47])=[O:45]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 67238656tert-Butyl (1R,2S)-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)cyclohexylcarbamate

Produkt 2

HCID 6422Trifluoroacetic acidHCID 53252276Mivavotinib

Versuchsvorschrift

A solution of cis-tert-butyl 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)cyclohexylcarbamate (109 mg, 0.183 mmol) in TFA (5 mL) was heated at 60° C. for 2 h. After removal of the solvent, the residue was diluted in MeOH (2 mL) and was purified by preparative HPLC. The fractions were collected and stripped to dryness via rotary evaporation to give the title compound as a TFA salt. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.47 (br s, 2 H), 1.57-1.75 (m, 3 H), 1.84 (br s, 2 H), 3.12-3.23 (m, 2 H), 3.87-3.94 (m, 3 H), 4.35-4.50 (m, 3 H), 6.73 (br s, 1 H), 7.71 (br s, 2 H), 8.28-8.44 (m, 2 H), 8.84 (d, J=3.91 Hz, 1 H). [M+H] calc'd for C17H21FN6O, 345; found, 345.

Aufarbeitung

  1. customAfter removal of the solvent
  2. additionthe residue was diluted in MeOH (2 mL)
  3. customwas purified by preparative HPLC
  4. customThe fractions were collected
  5. customstripped to dryness via rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-0a5cbf448db04658907492665b258afd
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108970B2

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