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Diisopropylamine → 6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide

HRID 724226
ノート
印刷プレビュー

反応式

HRID 724226 の反応式
[CH:1](NC(C)C)([CH3:3])[CH3:2].[CH2:8]([Li])[CH2:9]CC.C(OCC)(=O)C.[CH:19]([N:22](C(C)C)[C:23]([C:25]1C=C[C:32]2[C:27](=C[CH:29]=[C:30]([C:35]([C:37]3[N:38]=[CH:39][N:40](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:41]=3)=[O:36])[CH:31]=2)[CH:26]=1)=[O:24])(C)C>C1COCC1.O>[OH:36][C:35]1([C:30]2[CH:31]=[C:32]3[C:1](=[CH:3][CH:29]=2)[CH:2]=[C:25]([C:23]([NH:22][CH3:19])=[O:24])[CH:26]=[CH:27]3)[C:37]2[N:38]([CH:39]=[N:40][CH:41]=2)[CH2:9][CH2:8]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 21879613N,N-diisopropyl-6-[(1-trityl-1H-imidazol-4-yl)carbonyl]-2-naphthamideHCID 178418339Butyllithium

生成物 1

HCID 98830296-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-70 °C

実験手順

Dry THF (600 ml) containing diisopropylamine (21.3 ml) was cooled to −70° C. and n-butyl lithium (1.6 M; 95.0 ml) was added dropwise. The mixture was stirred for 10 min and ethyl acetate (14.9 ml) was added dropwise. The mixture was stirred at the same temperature for 30 min. A solution of N,N-diisopropyl-6-[(1-trityl-1H-imidazol-4-yl)carbonyl]-2-naphthamide (60.0 g) in dry THF (150 ml) was added dropwise at −70° C. The mixture was stirred at the same temperature for 30 min and the reaction mixture was gradually warmed to −30° C. Water was added to stop the reaction. The organic layer was separated and the aqueous layer was extracted with a THF-toluene (1:1) mixture. The organic layers were combined, washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated to give the title compound quantitatively as a pale yellow oil.

後処理

  1. stirringThe mixture was stirred at the same temperature for 30 min
  2. stirringThe mixture was stirred at the same temperature for 30 min
  3. temperaturethe reaction mixture was gradually warmed to −30° C
  4. customthe reaction
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with a THF-toluene (1:1) mixture
  7. washwashed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-9e33f6d1aeae4927a2acf4fea78309bc
出典データセット
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07141598B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート