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

HRID 72077노트

반응식

HRID 72077 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6a4de6b4e4cd4454885627d06a9b4779
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828429B2

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