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Trimethyl orthovalerate → 1,1-dimethylethyl N-[4-(2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]carbamate

HRID 47475
ノート
印刷プレビュー

反応式

HRID 47475 の反応式
[C:1](OC)(OC)(OC)[CH2:2][CH2:3][CH2:4][CH3:5].[NH2:12][C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:22]=1[NH:23][CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[N:20][CH:19]=[CH:18][CH:17]=2.O.C1(C)C=CC(S(OS(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[CH2:2]([C:1]1[N:23]([CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:32])([CH3:34])[CH3:33])[C:22]2[C:21]3[N:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:12]=1)[CH2:3][CH2:4][CH3:5]
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 3

HCID 83755Trimethyl orthovalerateHCID 22172729Tert-butyl 4-[(3-amino[1,5]naphthyridin-4-yl)amino]butylcarbamateHCID 22172731p-Toluene sulfonic anhydride hydrate

生成物 1

HCID 221727131,1-dimethylethyl N-[4-(2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]carbamate

試薬・触媒・溶媒 2

HCID 7237O-Xylene溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

Freshly distilled trimethyl orthovalerate (41 mL, 0.24 mole) was added to a mixture of 1,1-dimethylethyl N-{4-[(3-amino[1,5]naphthyridin-4-yl)amino]butyl}carbamate (39 g, 0.12 mole) in warm xylene (500 mL). The reaction mixture was heated at reflux overnight. Thin layer chromatography showed that at least half of the starting material was still present. p-Toluenesulfonic anhydride monohydrate (6 g) was added. After a short time thin layer chromatography showed that the reaction was complete. The reaction mixture was allowed to cool to ambient temperature and then it was diluted with ethyl acetate and washed with aqueous sodium bicarbonate. The organic layer was concentrated under vacuum to provide an oily residue. The residue was triturated with hexane to provide a dark pink solid. This solid was recrystallized from acetonitrile to provide 1,1-dimethylethyl N-[4-(2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]carbamate as a pale peach solid, m.p. 96.0-98.0° C. Analysis: Calculated for C22H31N5O2: %C, 66.47; %H, 7.86; %N, 17.62. Found: %C, 66.29; %H, 7.78; %N, 17.76.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. washwashed with aqueous sodium bicarbonate
  4. concentrationThe organic layer was concentrated under vacuum
  5. customto provide an oily residue
  6. customThe residue was triturated with hexane
  7. customto provide a dark pink solid
  8. customThis solid was recrystallized from acetonitrile

出典と根拠

ORDレコード
ord-81dee845455f458cadfc37fd0ec66106
出典データセット
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06699878B2

反応ノート

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