Trifluoroacetic acid → HCID 178496842, 화합물

HRID 539923노트

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HRID 539923 반응식
[Cl:1][C:2]1[C:3]([NH:37][CH:38]2[CH:43]3[CH2:44][CH2:45][CH:40]([CH2:41][CH2:42]3)[CH:39]2[C:46]([O:48][CH3:49])=[O:47])=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=2)=[N:6][CH:7]=1.[SiH](CC)(CC)CC.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([NH:37][CH:38]2[CH:43]3[CH2:42][CH2:41][CH:40]([CH2:45][CH2:44]3)[CH:39]2[C:46]([O:48][CH3:49])=[O:47])=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[NH:10][N:9]=2)=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86707193methyl 3-((5-chloro-2-(5-fluoro-1-trityl-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-yl)amino)bicyclo[2.2.2]octane-2-carboxylate

생성물 1

HCID 178496842HCID 178496842, 화합물수율 66%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (+/−)-trans-(2,3)-methyl 3-((5-chloro-2-(5-fluoro-1-trityl-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-yl)amino)bicyclo[2.2.2]octane-2-carboxylate, 38, (0.85 g, 1.26 mmol) in CH2Cl2 (42.5 mL) at room temperature was added Et3SiH (1.00 mL, 6.32 mmol) followed by trifluoroacetic acid (0.97 mL, 12.60 mmol). The reaction was stirred at room temperature. After the reaction was complete, as judged by LC-MS, the solution was concentrated in vacuo. Careful flash chromatography (SiO2, 0-7% MeOH—CH2Cl2, gradient elution) provided the desired product (373 mg, 66% yield)L 1H NMR (400 MHz, MeOD) δ 8.66 (dd, J=8.3, 2.5 Hz, 1H), 8.53 (s, 1H), 8.28 (s, 1H), 5.05 (d, J=6.5 Hz, 1H), 3.69 (s, 3H), 2.95 (d, J=6.8 Hz, 1H), 2.09 (s, 1H), 1.98 (s, 1H), 1.96-1.79 (m, 3H), 1.77-1.61 (m, 3H), 1.61-1.45 (m, 2H); LC/MS Gradient 10-90%, 0.1% formic 5 min, C18/ACN, RT=2.55 min, (M+H) 431.14.

후처리

  1. concentrationthe solution was concentrated in vacuo
  2. washCareful flash chromatography (SiO2, 0-7% MeOH—CH2Cl2, gradient elution)

출처 및 근거

ORD 기록
ord-0129d3f8c762468196d285fdf8781f05
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871774B2

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