Trifluoroacetic acid → HCID 178434451, 화합물

HRID 2241215노트

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[F:1][C:2]1[CH:3]=[C:4]([NH:28][C:29]([C:31]2[C:32](=[O:44])[N:33]([C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)[CH:34]=[CH:35][CH:36]=2)=[O:30])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[N:15](CC3C=CC(OC)=CC=3)[N:16]=[C:17]([CH3:18])[C:10]=12.C(O)(C(F)(F)F)=O>>[F:1][C:2]1[CH:3]=[C:4]([NH:28][C:29]([C:31]2[C:32](=[O:44])[N:33]([C:37]3[CH:38]=[CH:39][C:40]([F:43])=[CH:41][CH:42]=3)[CH:34]=[CH:35][CH:36]=2)=[O:30])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[NH:15][N:16]=[C:17]([CH3:18])[C:10]=12

참가 물질

반응물 2

HCID 6422Trifluoroacetic acid

HCID 68516431N-(3-fluoro-4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

생성물 1

HCID 178434451HCID 178434451, 화합물수율 74%

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온도: 50 °C

실험 절차

A mixture of N-(3-fluoro-4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (0.045 g, 0.0758 mmol) and TFA (0.58 mL, 7.58 mmol) was placed in a vial and heated at 50° C. for 4 hours. The reaction mixture was concentrated under reduced pressure using toluene to azeotrope. The crude was treated with THF and Et3N and purified by silica gel flash column chromatography (2% MeOH in CH2Cl2) to afford 26.5 mg (74%) of the desired product. LRMS (ESI pos) m/e 474.2 (M+1). 1H-NMR (400 MHz, CD3OD/CDCl3) δ 8.72 (dd, 1H), 8.24 (d, 1H), 7.99 (dd, 1H), 7.92 (dd, 1H), 7.51 (m, 2H), 7.42 (m, 1H), 7.32 (t, 3H), 6.75 (t, 1H), 6.26 (d, 1H), 2.73 (s, 3H); 19F NMR (376 MHz, CD3OD/CDCl3) δ −113.2, −128.8.

후처리

concentrationThe reaction mixture was concentrated under reduced pressure
additionThe crude was treated with THF and Et3N
custompurified by silica gel flash column chromatography (2% MeOH in CH2Cl2)

출처 및 근거

ORD 기록: ord-4a82b465709f431fac61b5e17ed8f09a
출처 데이터셋: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07723330B2

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