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Pyridine → N-(6-ethyl-5-((2'-methyl-[2,4'-bipyridin]-4-yl)oxy)pyridin-2-yl)-2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamide

HRID 2279010
ノート
印刷プレビュー

反応式

HRID 2279010 の反応式
[O:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:11][CH2:10][NH:9][C:8]2=[O:12])[CH2:3][CH2:2]1.N1C=CC=CC=1.[C:19](Cl)(Cl)=[O:20].[CH2:23]([C:25]1[N:30]=[C:29]([NH2:31])[CH:28]=[CH:27][C:26]=1[O:32][C:33]1[CH:38]=[CH:37][N:36]=[C:35]([C:39]2[CH:44]=[CH:43][N:42]=[C:41]([CH3:45])[CH:40]=2)[CH:34]=1)[CH3:24]>C(Cl)Cl>[CH2:23]([C:25]1[N:30]=[C:29]([NH:31][C:19]([N:9]2[CH2:10][CH2:11][N:7]([CH:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)[C:8]2=[O:12])=[O:20])[CH:28]=[CH:27][C:26]=1[O:32][C:33]1[CH:38]=[CH:37][N:36]=[C:35]([C:39]2[CH:44]=[CH:43][N:42]=[C:41]([CH3:45])[CH:40]=2)[CH:34]=1)[CH3:24]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1049Pyridine2 回HCID 6371PhosgeneHCID 904259751-(Oxan-4-yl)imidazolidin-2-oneHCID 904275116-Ethyl-5-((2'-methyl-[2,4'-bipyridin]-4-yl)oxy)pyridin-2-amine

生成物 1

HCID 86269027N-(6-ethyl-5-((2'-methyl-[2,4'-bipyridin]-4-yl)oxy)pyridin-2-yl)-2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamide収率 4%

試薬・触媒・溶媒

1
HCID 6344Dichloromethane溶媒2 回

実験手順

A 0° C. solution of Example B1 (0.19 g, 1.116 mmol) and pyridine (0.26 mL, 3.21 mmol) in DCM (5 mL) was treated drop-wise with phosgene (20% in toluene, 1.4 mL, 2.65 mmol), warmed to RT over 0.5 h, then treated slowly with a solution of 6-ethyl-5-((2′-methyl-[2,4′-bipyridin]-4-yl)oxy)pyridin-2-amine (0.13 g, 0.424 mmol) and pyridine (0.16 mL, 1.978 mmol) in DCM (5 mL) and stirred at RT overnight. The mixture was treated with satd. NaHCO3, extracted with EtOAc (4×) and the combined organics were dried over MgSO4, concentrated to dryness, purified via silica gel chromatography (MeOH/DCM), then re-purified via reverse-phase chromatography (MeCN/H2O with 0.1% TFA). The organics were removed under reduced pressure, the aqueous residue treated with satd. NaHCO3, extracted with DCM (5×) and the combined organics were dried over MgSO4 and concentrated to dryness to afford N-(6-ethyl-5-((2′-methyl-[2,4′-bipyridin]-4-yl)oxy)pyridin-2-yl)-2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamide (8 mg, 4%). 1H NMR (400 MHz, DMSO-d6): δ 10.93 (s, 1 H), 8.56 (d, J=5.7 Hz, 1 H), 8.52 (d, J=5.3 Hz, 1 H), 7.93-7.89 (m, 2 H), 7.67 (d, J=2.4 Hz, 1 H), 7.68-7.66 (m, 1 H), 7.64 (s, 1 H), 6.86 (dd, J=5.7, 2.4 Hz, 1 H), 3.94-3.78 (m, 5 H), 3.49-3.34 (m, 4 H), 2.58 (q, J=7.5 Hz, 2 H), 2.53 (s, 3H), 1.78-1.66 (m, 2 H), 1.64-1.57 (m, 2 H), 1.12 (t, J=7.5 Hz, 3H); MS (ESI) m/z: 503.3 (M+H+).

後処理

  1. additionThe mixture was treated with satd
  2. extractionNaHCO3, extracted with EtOAc (4×)
  3. dry with materialthe combined organics were dried over MgSO4
  4. concentrationconcentrated to dryness
  5. custompurified via silica gel chromatography (MeOH/DCM)
  6. customre-purified via reverse-phase chromatography (MeCN/H2O with 0.1% TFA)
  7. customThe organics were removed under reduced pressure
  8. additionthe aqueous residue treated with satd
  9. extractionNaHCO3, extracted with DCM (5×)
  10. dry with materialthe combined organics were dried over MgSO4
  11. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-ecf5ffee391047959ff95cdca2bafa71
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09133183B2

反応ノート

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