1H-Indole-5-Carboxylic Acid → 1h-Indole-5-carboxamide,n-(cyclopentylmethyl)-

HRID 728597

反応式

HRID 728597 の反応式
[CH:1]1([CH2:6][NH2:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)(O)=[O:9].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[CH:1]1([CH2:6][NH:7][C:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[CH:14]3)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 742801H-Indole-5-Carboxylic AcidHCID 80153CyclopentanemethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 100373961h-Indole-5-carboxamide,n-(cyclopentylmethyl)-収率 80%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of cyclopentylmethylamine (2.66 g), 5-carboxyindole (4.76 g), 4-(dimethylamino)pyridine (3.60 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.67 g) in dichloromethane (60 ml) was stirred for 12 hours under an atmosphere of nitrogen. The amber solution was diluted with dichloromethane (150 ml), washed successively with 10% (w/v) aqueous sodium carbonate, 10% (v/v) hydrochloric acid, water, and brine, dried (MgSO4), and evaporated. The residual amber oil was purified by flash chromatography on silica gel (700 ml), eluting with 1:3 v/v ethyl acetate:chloroform, to yield 5-(N-cyclopentylmethylcarbamoyl)indole (A) (5.17 g, 80%) as a white crystalline solid; mp 110°-112° C.; NMR (80 MHz, CDCl3): 1.0-2.4(broad m, 9H, cyclopentyl), 3.4(dd, 2H, CH2N), 6.2(broad, 1H, NH), 6.6(m, 1H, H3 -indole), 7.3(t, 1H, H2 -indole), 7.4(d, 1H, H7 -indole), 8.5(broad, 1H, CONH).

後処理

  1. washwashed successively with 10% (w/v) aqueous sodium carbonate, 10% (v/v) hydrochloric acid, water, and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residual amber oil was purified by flash chromatography on silica gel (700 ml)
  5. washeluting with 1:3 v/v ethyl acetate

出典と根拠

ORDレコード
ord-d06b1ddac7024f6fb51234454273df9c
出典データセット
uspto-grants-1991_09
特許番号
US05049576

関連ノート

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