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

HRID 724225ノート

反応式

HRID 724225 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.Cl.C([N:26]=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.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]([NH2:26])=[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

6

反応物 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 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]imidazol-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 reaction mixture was warmed to room temperature and stirred for 18 h. Silica gel (3 g) was added to the reaction mixture and the mixture was concentrated to dryness under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol containing aqueous ammonia (7%): 19/1) and the eluate was concentrated to dryness. The residue was recrystallized from ethanol to give the title compound (53 mg).

後処理

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

出典と根拠

ORDレコード
ord-30de7ef3470c4e8ebb77b82b1b0250b7
出典データセット
uspto-grants-2006_11
特許番号
US07141598B2

反応ノート

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