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1-Hydroxybenzotriazole → 3-amino-5-(4-fluorophenyl)-N-{2-[4-(1-pyrrolidin-1-ylethyl)phenyl]ethyl}thiophene-2-carboxamide

HRID 1668398
ノート
印刷プレビュー

反応式

HRID 1668398 の反応式
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:14]([OH:16])=O.Cl.Cl.[N:19]1([CH:24]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][NH2:34])=[CH:28][CH:27]=2)[CH3:25])[CH2:23][CH2:22][CH2:21][CH2:20]1.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC>C(OCC)(=O)C.CN(C=O)C>[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=2)[S:4][C:3]=1[C:14]([NH:34][CH2:33][CH2:32][C:29]1[CH:28]=[CH:27][C:26]([CH:24]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH3:25])=[CH:31][CH:30]=1)=[O:16]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 107523413-amino-5-(4-fluorophenyl)thiophene-2-carboxylic AcidHCID 673611332-[4-(1-Pyrrolidin-1-ylethyl)phenyl]ethanamine dihydrochloride

生成物 1

HCID 67359464
3-amino-5-(4-fluorophenyl)-N-{2-[4-(1-pyrrolidin-1-ylethyl)phenyl]ethyl}thiophene-2-carboxamide
収率 45.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 3-amino-5-(4-fluorophenyl)thiophene-2-carboxylic acid (0.20 g), 2-[4-(1-pyrrolidin-1-ylethyl)phenyl]ethanamine dihydrochloride (0.22 g), 1-hydroxybenzotriazole (0.16 g), N,N-diisopropylethylamine (0.30 ml) and DMF (3.0 ml) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.15 g), and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (hexane:ethyl acetate=9:1 (volume ratio)→1:2 (volume ratio)) using NH-silica gel to give 3-amino-5-(4-fluorophenyl)-N-{2-[4-(1-pyrrolidin-1-ylethyl)phenyl]ethyl}thiophene-2-carboxamide (0.15 g).

後処理

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography (hexane

出典と根拠

ORDレコード
ord-f6ac35febcb84dc6a03849c474b84cf2
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07989445B2

反応ノート

読み込み中…

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