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Hydrochloric Acid → (trans)-4-(2-(7-(2-Methoxvethoxv)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)pyrrolidin-3-ol

HRID 1095708
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HRID 1095708 반응식
[OH:1][C@H:2]1[C@H:6]([O:7][C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[N:16]=[C:15]([C:18]2[N:22]4[CH:23]=[CH:24][C:25]([O:27][CH2:28][CH2:29][O:30][CH3:31])=[CH:26][C:21]4=[N:20][CH:19]=2)[CH:14]=[CH:13]3)[CH2:5][N:4](C(OCC2C=CC3C(=CC=CC=3)C=2)=O)[CH2:3]1.CCO.Cl>[Pd].C1COCC1>[CH3:31][O:30][CH2:29][CH2:28][O:27][C:25]1[CH:24]=[CH:23][N:22]2[C:18]([C:15]3[CH:14]=[CH:13][C:12]4[C:17](=[C:8]([O:7][C@@H:6]5[CH2:5][NH:4][CH2:3][C@H:2]5[OH:1])[CH:9]=[CH:10][CH:11]=4)[N:16]=3)=[CH:19][N:20]=[C:21]2[CH:26]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 131729511(trans)-Naphthalen-2-ylmethyl 3-hydroxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)pyrrolidine-1-carboxylate

생성물 1

HCID 25098433(trans)-4-(2-(7-(2-Methoxvethoxv)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)pyrrolidin-3-ol수율 20.2%

시약·촉매·용매 2

HCID 23938
Palladium
촉매
HCID 8028Tetrahydrofuran용매

실험 절차

A 25 mL flask was charged with (trans)-naphthalen-2-ylmethyl 3-hydroxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)pyrrolidine-1-carboxylate (0.100 g, 0.165 mmol), EtOH (1.6 mL), THF (1.6 mL), 2 N HCl (0.2 mL) and 10% Degussa type Pd/C (0.018 g, 0.017 mmol), and the reaction was placed under a balloon of H2 and stirred for 2 hours. The reaction was filtered (GF/F paper), the filter paper was washed with 2 N HCl and THF, the aqueous phase was washed with DCM, neutralized with saturated NaHCO3, and then extracted with DCM. The organic layer was dried and condensed to afford 14 mg of the desired product. MS APCI (+) m/z 421.2 (M+1) detected.

후처리

  1. filtrationThe reaction was filtered (GF/F paper)
  2. washthe filter paper was washed with 2 N HCl and THF
  3. washthe aqueous phase was washed with DCM
  4. extractionextracted with DCM
  5. customThe organic layer was dried
  6. customcondensed

출처 및 근거

ORD 기록
ord-7caf852f20864c8c885edf583a0ba40a
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08138181B2

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