P,P-Diphenylphosphinic azide → HCID 86721002、化合物

HRID 524944ノート

反応式

HRID 524944 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:17][C:16]2[CH:15]=[N:14][CH:13]=[C:12](C(O)=O)[C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P([N:35]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN1C(=O)CCC1>[NH2:35][C:12]1[CH:13]=[N:14][CH:15]=[C:16]2[C:11]=1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:17]2

参加物

4

反応物 2

HCID 199401P,P-Diphenylphosphinic azideHCID 847148112,7-Naphthyridine-2,5(1H)-dicarboxylic acid, 3,4-dihydro-, 2-(1,1-dimethylethyl) ester

生成物 1

HCID 86721002HCID 86721002、化合物

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
90 °C

実験手順

To a solution of 7-tert-butoxycarbonyl-6,8-dihydro-5H-2,7-naphthyridine-4-carboxylic acid (440 mg, 1.581 mmol) in NMP (6 mL) was added TEA (207.9 mg, 286.4 μL, 2.055 mmol) followed by diphenylphosphoryl azide (478.6 mg, 374.8 μL, 1.739 mmol) at rt under nitrogen. The reaction was heated to 90° C. for 2 hours. At RT, the reaction mixture was partitioned between an aqueous saturated solution of NaHCO3 and EtOAc. Combined organic extract was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica, eluting with 1-15% MeOH:DCM to yield tert-butyl 5-amino-3,4-dihydro-2,7-naphthyridine-2(1H)-carboxylate. (397 mg, 100.7%). MS (2ES+) 501.2.

後処理

  1. customAt RT, the reaction mixture was partitioned between an aqueous saturated solution of NaHCO3 and EtOAc
  2. extractionCombined organic extract
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica
  7. washeluting with 1-15% MeOH

出典と根拠

ORDレコード
ord-d0895b005fc84497a3cf56ce1016a9ca
出典データセット
uspto-grants-2016_05
特許番号
US09340546B2

反応ノート

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