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

HRID 72077ノート

反応式

HRID 72077 の反応式
[OH:1][C:2]1([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[C:15]([C:20](O)=[O:21])[CH:14]=[CH:13]3)[C:9]2[N:5]([CH:6]=[N:7][CH:8]=2)[CH2:4][CH2:3]1.C([N:25]=C=NCCCN(C)C)C.Cl.C(N(C(C)C)CC)(C)C>CN(C=O)C>[OH:1][C:2]1([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[C:15]([C:20]([NH2:25])=[O:21])[CH:14]=[CH:13]3)[C:9]2[N:5]([CH:6]=[N:7][CH:8]=2)[CH2:4][CH2:3]1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 218796156-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole-7-yl)-2-naphthoic acid

生成物 1

HCID 99658856-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-2-naphthamide収率 11.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole-7-yl)-2-naphthoic acid (449 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide•hydrochloride (321 mg) and 1-hydroxy-1H-benzotriazole•monohydrate (301 mg) were dissolved in DMF (7.6 ml), and diisopropylethylamine (216 mg) was added with stirring under ice cooling. The mixture was allowed to warm to room temperature and stirred for 18 hr. Silica gel (3 g) was added to the reaction mixture and the mixture was concentrated under reduced pressure to dryness. The obtained residue was purified by silica gel column chromatography (developing solution: chloroform/7% aqueous ammonia-containing methanol:19/1). The eluate was concentrated to dryness, and the residue was recrystallized from ethanol to give the title compound (53 mg).

後処理

  1. stirringstirred for 18 hr
  2. additionSilica gel (3 g) was added to the reaction mixture
  3. concentrationthe mixture was concentrated under reduced pressure to dryness
  4. customThe obtained residue was purified by silica gel column chromatography (developing solution: chloroform/7% aqueous ammonia-containing methanol:19/1)
  5. concentrationThe eluate was concentrated to dryness
  6. customthe residue was recrystallized from ethanol

出典と根拠

ORDレコード
ord-6a4de6b4e4cd4454885627d06a9b4779
出典データセット
uspto-grants-2014_09
特許番号
US08828429B2

反応ノート

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