Lithium Hydroxide → 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(3-fluorophenyl)-2-pyrimidinamine

HRID 1159884Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1159884
FC(F)(F)C([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=4)[N:22]=3)=[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][N:14]3[N:13]=2)[CH:7]=1)=O.[OH-].[Li+]>C1COCC1.O>[NH2:5][C:6]1[CH:7]=[C:8]([C:12]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=4)[N:22]=3)=[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][N:14]3[N:13]=2)[CH:9]=[CH:10][CH:11]=1

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 595138292,2,2-Trifluoro-N-[3-(3-{2-[(3-fluorophenyl)amino]-4-pyrimidinyl}pyrazolo-[1,5-a]pyridin-2-yl)phenyl]acetamide

Produkt 1

HCID 595114034-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(3-fluorophenyl)-2-pyrimidinamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2,2,2-trifluoro-N-(3-{3-[2-(3-fluoro-phenylamino)-pyrimidin-4-yl]-pyrazolo[1,5-a]pyridin-2-yl}-phenyl)-acetamide (2.15 g, 4.4 mmol) and lithium hydroxide (277 mg, 6.6 mmol) in THF (44 mL) and water (10 mL) was stirred for 16 h. The reaction was extracted with DCM. The combined organic phases were dried over MgSO4 and purified through silica gel to give the title compound as a white solid. 1H NMR (400 MHz, d6-DMSO): δ 9.75 (s, 1H), 8.78 (d, J=6.8 Hz, 1H), 8.52 (d, J=9.2 Hz, 1H), 8.25 (d, J=5.6 Hz, 1H), 7.80 (d, J=12.4 Hz, 1H), 7.47-7.43 (m, 2H), 7.29-7.23 (m, 1H), 7.12-7.06 (m, 2H), 6.77 (s, 1H), 6.71 (dt, J=8.4 and 2.4 Hz, 1H), 6.66-6.62 (m, 2H), 6.54 (d, J=5.6 Hz, 1H), 5.21 (s, 2H) ppm. HRMS calculated C23H17FN6 [M+H]+ 397.1577 found 397.1558.

Aufarbeitung

  1. extractionThe reaction was extracted with DCM
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. custompurified through silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a8fd79a0571f4466bbfa8da77732e6d9
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812022B2

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