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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 1-(5-Chloroindol-2-ylsulphonyl)-4-[6-(4-pyridyl)nicotinoyl]piperazine

HRID 2085914
ノート
印刷プレビュー

反応式

HRID 2085914 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][N:8]=2)=[CH:3][CH:2]=1.[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([S:26]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)(=[O:28])=[O:27])=[CH:20]2.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([S:26]([N:29]1[CH2:34][CH2:33][N:32]([C:11](=[O:13])[C:10]3[CH:14]=[CH:15][C:7]([C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)=[N:8][CH:9]=3)[CH2:31][CH2:30]1)(=[O:28])=[O:27])=[CH:20]2
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22709453[2,4'-Bipyridine]-5-carboxylic acidHCID 227105715-chloro-2-(piperazine-1-sulfonyl)-1H-indole

生成物 1

HCID 98913881-(5-Chloroindol-2-ylsulphonyl)-4-[6-(4-pyridyl)nicotinoyl]piperazine収率 70.5%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒
2 回

実験手順

A stirred suspension of 6-(4-pyridyl)nicotinic acid (400 mg, 2 mmol) in dimethylformamide, DMF, (10 ml) was treated with 1-(5-chloroindol-2-ylsulphonyl)piperazine (600 mg, 2 mmol, 1 mol eq.) and 1-(3-dimethylaminopropyl)-3-ethylcarbodi-imide hydrochloride (EDAC, 460 mg, 2.4 mmol, 1.2 mol eq.). After stirring overnight the solvent was removed in vacuo and the residue chromatographed (Isolute 20 g silica cartridge, eluting with dichloromethane containing 2.5%-5% v/v of methanol) to yield 1-(5-chloroindol-2-ylsulphonyl)-4-[6-(4-pyridyl)nicotinoyl]piperazine as a colourless foam (680 mg). This was dissolved in dichloromethane/methanol mixture (40 ml of 1:1) and treated with a saturated solution of HCI in methanol until acid to indicator paper (slight excess). The resulting solution of hydrochloride salt was evaporated to dryness and the residue boiled in 2-propanol (100 ml, incomplete solution). Filtration and cooling gave 1-(5-chloroindol-2-ylsulphonyl)-4-[6-(4-pyridyl)nicotinoyl]piperazine hydrochloride as a colourless solid, (220 mg), 1H NMR (d6-DMSO) 3.0-3.3 (broad d, 4H), 3.6-4.0 (broad d, 4H), 7.05 (s, 1H), 7.35 (dd, 1H), 7.5 (d, 1H), 7.8 (d, 1H), 8.1 (dd, 1H), 8.35 (d, 1H), 8.5 (m, 2H), 8.8 (d, 1H), 8.95 (d, 2H), 12.4 (s, 1H), signals were also present due to 2-propanol (0.5 mol equiv.); MS (M+H)+ 481/483; mp 186-190° C. (not sharp).

後処理

  1. customwas removed in vacuo
  2. customthe residue chromatographed (Isolute 20 g silica cartridge
  3. washeluting with dichloromethane containing 2.5%-5% v/v of methanol)

出典と根拠

ORDレコード
ord-9aa1dd140299491290fd1113bb771799
出典データセット
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06723723B1

反応ノート

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