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Lithium hydroxide, monohydrate → HCID 178427251, 화합물

HRID 2171910
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HRID 2171910 반응식
[F:1][C:2]1[C:3]([NH:18][CH:19]([C:26]2([CH3:31])[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:20][C:21]([O:23]CC)=[O:22])=[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.O.[OH-].[Li+]>C1COCC1.O>[F:1][C:2]1[C:3]([NH:18][CH:19]([C:26]2([CH3:31])[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:20][C:21]([OH:23])=[O:22])=[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
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참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 178471969HCID 178471969, 화합물2회

생성물 1

HCID 178427251HCID 178427251, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

To a solution of racemic ethyl 3-[[5-fluoro-2-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-yl]amino]-3-(1-methylcyclopentyl)propanoate, 149a, (0.110 g, 0.256 mmol) in THF (30 mL) was added a solution of lithium hydroxide hydrate (0.043 g, 1.022 mmol) in H2O (20 mL). The reaction mixture was stirred at 70° C. overnight. The organic solvent was removed under reduced pressure and the remaining aqueous phase was used directly in the purification via preparatory HPLC. The resulting HPLC fractions were extracted with EtOAc. The organic phase was dried over MgSO4, filtered and the solvent was removed under reduced pressure to afford the desired product: 1H NMR (400 MHz, MeOD) δ 8.64 (dd, J=8.4, 2.4 Hz, 1H), 8.57 (s, 1H), 8.24 (d, J=4.4 Hz, 1H), 5.19 (d, J=8.7 Hz, 1H), 2.78 (qd, J=15.9, 6.6 Hz, 2H), 1.85-1.57 (m, 6H), 1.48 (dd, J=11.8, 6.0 Hz, 1H), 1.36 (dt, J=12.0, 6.0 Hz, 1H), 1.11 (s, 3H). LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, Retention Time=2.37 min, (M+H) 403.22.

후처리

  1. customThe organic solvent was removed under reduced pressure
  2. customthe remaining aqueous phase was used directly in the purification via preparatory HPLC
  3. extractionThe resulting HPLC fractions were extracted with EtOAc
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-c3bfa5ca202b4907b385753cc5dd9f68
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09051319B2

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