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Ethyl Acetate → 4-{6-Amino-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-3-yl}-piperidine-1-carboxamide

HRID 911999
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HRID 911999 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([C:11]3[CH2:12][CH2:13][N:14]([C:17]([NH2:19])=[O:18])[CH2:15][CH:16]=3)=[CH:9][O:10][C:4]=2[C:3]=1[O:20][C@@H:21]([C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[C:25]([F:30])[C:24]=1[Cl:31])[CH3:22].CCOC(C)=O>[Pd].CO>[NH2:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([CH:11]3[CH2:12][CH2:13][N:14]([C:17]([NH2:19])=[O:18])[CH2:15][CH2:16]3)=[CH:9][O:10][C:4]=2[C:3]=1[O:20][C@@H:21]([C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[C:25]([F:30])[C:24]=1[Cl:31])[CH3:22]
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참가 물질

5

반응물 2

HCID 8857Ethyl AcetateHCID 441816544-{6-Amino-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-furo[3,2-c]pyridin-3-yl}-3,6-dihydro-2H-pyridine-1-carboxamide

생성물 1

HCID 578123434-{6-Amino-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-3-yl}-piperidine-1-carboxamide

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol
용매

실험 절차

A mixture of 4-{6-amino-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridine-3-yl}-3,6-dihydro-2H-pyridine-1-carboxamide (17.0 mg, 0.037 mmol), palladium 10% wt on activated carbon (10 mg), EtOAc (4 mL) and MeOH (0.4 mL) was flushed with nitrogen, then a hydrogen (0.5 L) balloon was added, and the mixture was stirred at rt for 3 h. The suspension was filtered through a syringe filter pad, and the filtrate was concentrated in vacuo. The material was redissolved in MeOH (0.5 mL) and purified via HPLC. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=1.55-1.69 (m, 2H), 1.87 (d, J=6.8 Hz, 3H), 1.98-2.06 (m, 2H), 2.89-3.03 (m, 3H), 4.11 (d, J=12.9 Hz, 2H), 6.53 (q, J=6.7 Hz, 1H), 7.18-7.25 (m, 1H), 7.37-7.43 (m, 2H), 8.02 (s, 1H). MS (ES+): m/z 467.01/469.00 (100/69) [MH+]. HPLC: tR=2.58 min (ZQ3, polar—5 min).

후처리

  1. customwas flushed with nitrogen
  2. additiona hydrogen (0.5 L) balloon was added
  3. filtrationThe suspension was filtered through a syringe
  4. filtrationfilter pad
  5. concentrationthe filtrate was concentrated in vacuo
  6. dissolutionThe material was redissolved in MeOH (0.5 mL)
  7. custompurified via HPLC
  8. additionThe fractions containing the pure product
  9. concentrationwere concentrated in vacuo

출처 및 근거

ORD 기록
ord-77baab77cd8141dea17bb0193e0e7260
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08022206B2

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