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N-Hydroxyphthalimide → 2-[3-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propoxy]-1H-isoindole-1,3(2H)-dione

HRID 1187397
ノート
印刷プレビュー

反応式

HRID 1187397 の反応式
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH2:15]([C:18]1[N:19]([CH2:31][CH2:32][CH2:33][OH:34])[C:20]2[C:29]3[N:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:23]=[CH:22][C:21]=2[N:30]=1)[CH2:16][CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:55]1[C:59](=[O:60])[C:58]2=[CH:61][CH:62]=[CH:63][CH:64]=[C:57]2[C:56]1=[O:65]>O1CCCC1.C(OCC)(=O)C.ClCCl>[CH2:15]([C:18]1[N:19]([CH2:31][CH2:32][CH2:33][O:34][N:55]2[C:59](=[O:60])[C:58]3[C:57](=[CH:64][CH:63]=[CH:62][CH:61]=3)[C:56]2=[O:65])[C:20]2[C:29]3[N:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:23]=[CH:22][C:21]=2[N:30]=1)[CH2:16][CH3:17]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 685386673-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propan-1-ol

生成物 1

HCID 685404202-[3-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propoxy]-1H-isoindole-1,3(2H)-dione収率 103.8%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Diisopropyl azodicarboxylate (8.10 mL, 48.4 inmol) was added dropwise over ten minutes to a stirred solution of 3-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propan-1-ol (10.9 g, 40.3 mmol), triphenylphosphine (12.7 g, 48.4 mmol), and N-hydroxyphthalimide (7.89 g, 48.4 mmol) in tetrahydrofuran (160 mL) at 0° C. The reaction was allowed to warm to room temperature and was stirred overnight. The solvent was removed under reduced pressure to afford an oil that was dissolved in ethyl acetate (200 mL) and extracted with 2 M HCl (3×100 mL). The aqueous layers were combined, and the pH was adjusted to 7 with the addition of solid sodium bicarbonate. A precipitate formed, was isolated by filtration, and was dissolved in dichloromethane (300 mL). The solution was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 17.38 g of 2-[3-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propoxy]-1H-isoindole-1,3(2H)-dione as a tan solid.

後処理

  1. customThe solvent was removed under reduced pressure
  2. customto afford an oil that
  3. extractionextracted with 2 M HCl (3×100 mL)
  4. additionthe pH was adjusted to 7 with the addition of solid sodium bicarbonate
  5. customA precipitate formed
  6. customwas isolated by filtration
  7. dry with materialThe solution was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-b0819fbab05f4586b66978e08cc1986a
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08673932B2

反応ノート

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