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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
ノート
印刷プレビュー

反応式

HRID 911999 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol
溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-77baab77cd8141dea17bb0193e0e7260
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08022206B2

反応ノート

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