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

HRID 724210
ノート
印刷プレビュー

反応式

HRID 724210 の反応式
O[C:2]1([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[C:15]([C:20]([NH:22][CH3:23])=[O:21])[CH:14]=[CH:13]3)[C:9]2[N:5]([CH:6]=[N:7][CH:8]=2)[CH2:4][CH2:3]1.Cl.[H][H]>CO.[C].[Pd]>[CH:8]1[N:7]=[CH:6][N:5]2[CH2:4][CH2:3][CH:2]([C:10]3[CH:11]=[C:12]4[C:17](=[CH:18][CH:19]=3)[CH:16]=[C:15]([C:20]([NH:22][CH3:23])=[O:21])[CH:14]=[CH:13]4)[C:9]=12
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 313Hydrochloric AcidHCID 98830296-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 218796206-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide収率 72.6%

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒
HCID 887
Methanol
溶媒

実験手順

6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide (77 mg) was dissolved in methanol (5 ml). 1 N Hydrochloric acid (0.5 ml) and 10% palladium carbon (50% wet, 39 mg) were added, and the mixture was vigorously stirred for 12 h under 4 kg/cm2 hydrogen atmosphere. The catalyst was filtered off and the residue was washed with methanol. The filtrate and the washing were combined and aqueous potassium carbonate solution (0.25 M; 1 ml) was added. After neutralization, the solvent was evaporated under reduced pressure, and the residue was purified by flash silica gel column chromatography (eluent, chloroform/methanol containing ammonia (7%); 19/1). The eluate was recrystallized from chloroform-ether to give the title compound (53 mg) as colorless crystals.

後処理

  1. filtrationThe catalyst was filtered off
  2. washthe residue was washed with methanol
  3. additionaqueous potassium carbonate solution (0.25 M; 1 ml) was added
  4. customAfter neutralization, the solvent was evaporated under reduced pressure
  5. customthe residue was purified by flash silica gel column chromatography (eluent, chloroform/methanol containing ammonia (7%); 19/1)
  6. customThe eluate was recrystallized from chloroform-ether

出典と根拠

ORDレコード
ord-cc9348aa939140dba8294ace74a5f4a0
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

読み込み中…

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