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Ethyl Acetate → N-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenyl)-2-(4-fluorophenylamino)isonicotinamide

HRID 1670272
ノート
印刷プレビュー

反応式

HRID 1670272 の反応式
C(OC1C=[CH:13][C:12]([NH:15][C:16]2[N:21]=CN=[C:18]([O:22][C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:42])[CH2:31][C:32](NC4C=CC(F)=CC=4)=O)=[CH:25][C:24]=3[F:43])[CH:17]=2)=CC=1)C1C=CC=CC=1.CCO[C:47]([CH3:49])=O.C([O-])(O)=O.[Na+]>ClCCCl>[NH2:21][C:16]1[CH:17]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:42])[C:31]3[CH:32]=[CH:12][N:15]=[C:16]([NH:21][C:47]4[CH:49]=[CH:25][C:24]([F:43])=[CH:23][CH:28]=4)[CH:17]=3)=[CH:25][C:24]=2[F:43])[CH:13]=[CH:12][N:15]=1
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 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 59853038N-(4-(6-(4-(Benzyloxy)phenylamino)pyrimidin-4-yloxy)-3-fluorophenyl)-N3-(4-fluorophenyl)malonamide2 回

生成物 1

HCID 46851683N-(4-(2-Aminopyridin-4-yloxy)-3-fluorophenyl)-2-(4-fluorophenylamino)isonicotinamide収率 6.3%

試薬・触媒・溶媒 1

HCID 11
1,2-Dichloroethane
溶媒
2 回

実験手順

A solution of 4-(4-amino-2-fluorophenoxy)pyridine-2-amine (Compound B of Example 24, 450 mg, 2.1 mmol) in 1,2-dichloroethane (10 mL) was added slowly to a solution of acylchloride obtained above in 1,2-dichloroethane (10 mL) at ice bath temperature with stirring. The reaction mixture was allowed to stand at rt overnight. To the reaction mixture were added EtOAc (150 mL) and saturated aq. NaHCO3 solution (50 mL). The EtOAc layer was separated, dried over MgSO4 and concentrated in vacuo. The residue was purified by preparative HPLC to obtain the title compound (69 mg, 6.3%) as a yellow solid (bis-TFA salt). 1H NMR (DMSO-d6) δ 10.90 (s, 1H), 9.32 (s, 1H), 8.27 (d, 1H, J=5.5 Hz), 7.92-7.07 (m, 11H), 6.68 (dd, 1H, J=7.1, 2.2 Hz), 6.10 (d, 1H, J=2.2 Hz); MS (ESI+) m/z 217.9 (M+H)+.

後処理

  1. customThe EtOAc layer was separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-1cd0ec031eaf4f1380e74da61997c1d1
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07989477B2

反応ノート

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