1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178523145、化合物

HRID 1934729ノート

反応式

HRID 1934729 の反応式
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:10]=2[C:11]([OH:13])=O)[CH2:4][CH2:3]1.Cl.[F:22][C:23]([F:34])([F:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][CH2:31][NH2:32].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[OH:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:10]=2[C:11]([NH:32][CH2:31][CH2:30][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[C:23]([F:22])([F:33])[F:34])=[O:13])[CH2:6][CH2:7]1

参加物

6

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 224676532-[2-(Trifluoromethyl)phenyl]ethan-1-amine--hydrogen chloride (1/1)HCID 178524575HCID 178524575、化合物

生成物 1

HCID 178523145HCID 178523145、化合物収率 81.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 2-(cis-4-hydroxycyclohexylamino)-5-nitrobenzoic acid (120 mg), [2-(trifluoromethyl)phenyl]ethylamine hydrochloride (111 mg), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (86.4 mg) and 1-hydroxybenzotriazole (81.0 mg) in anhydrous dimethylformamide (3 mL) was stirred for 18 hours at ambient temperature. The mixture was partitioned between water and ethyl acetate. The separated organic layer was washed with IN-hydrochloric acid, water, an aqueous saturated sodium bicarbonate solution and brine, successively, and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by a preparative silica gel thin layer chromatography with a mixture of hexane and ethyl acetate (2:1). The obtained product was recrystallized from a mixture of petroleum ether and diethyl ether to give 2-(cis-4-hydroxycyclohexylamino)-5-nitro-N-{[2-(trifluoromethyl)phenyl]ethyl}benzamide (157 mg) as yellow powders.

後処理

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washThe separated organic layer was washed with IN-hydrochloric acid, water
  3. dry with materialan aqueous saturated sodium bicarbonate solution and brine, successively, and dried over magnesium sulfate
  4. customAfter evaporation of the solvent
  5. customthe residue was purified by a preparative silica gel thin layer chromatography with a mixture of hexane and ethyl acetate (2:1)
  6. customThe obtained product was recrystallized from a mixture of petroleum ether and diethyl ether

出典と根拠

ORDレコード
ord-36078cf1e4ea42a88b35753fbc190f4f
出典データセット
uspto-grants-2002_05
特許番号
US06384080B1

反応ノート

読み込み中…