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Pyrrolidine → 2-[4-(2-hydroxyethyl)piperazin-1-yl]-N-[2,4-bis(pyrrolidin-1-yl)-6-methylpyridin-3-yl]acetamide

HRID 227529
ノート
印刷プレビュー

反応式

HRID 227529 の反応式
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]([NH:13][C:14]2[C:15](Br)=[N:16][C:17]([CH3:21])=[CH:18][C:19]=2Br)=[O:12])[CH2:6][CH2:5]1.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>>[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]([NH:13][C:14]2[C:15]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[N:16][C:17]([CH3:21])=[CH:18][C:19]=2[N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:12])[CH2:6][CH2:5]1
参加物実験手順後処理出典と根拠反応ノート

参加物

3

反応物 2

HCID 31268PyrrolidineHCID 116406602-[4-(2-Hydroxyethyl)piperazin-1-yl]-N-[2,4-dibromo-6-methyl-3-pyridyl]acetamide

生成物 1

HCID 210873432-[4-(2-hydroxyethyl)piperazin-1-yl]-N-[2,4-bis(pyrrolidin-1-yl)-6-methylpyridin-3-yl]acetamide

実験手順

2-[4-(2-Hydroxyethyl)piperazin-1-yl]-N-[2,4-dibromo-6-methyl-3-pyridyl]acetamide (1.00 g, 2.29 mmol) was dissolved in pyrrolidine (10 mL), and the solution was subjected to reflux for 4 days. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to separation through silica gel column chromatography (developer: hexane:acetone=2:1), to thereby yield a crude product of 2-[4-(2-hydroxyethyl)piperazin-1-yl]-N-[2,4-bis(pyrrolidin-1-yl)-6-methyl-3-pyridyl]acetamide (1.22 g) as a brown foamed substance. The crude product was dissolved in pyridine (20 mL), and acetic anhydride (10 mL) was added thereto under cooling with ice, followed by stirrng for 14 hours at room temperature. The reaction mixture was concentrated under reduced pressure. Toluene (70 mL) was added to the residue and then evaporated three times, followed by purification through silica gel column chromatography (developer: chloroform:methanol=20:1→chloroform: ammonia-saturated methanol=50:1→chloroform:ammonia-saturated methanol=20:1), to thereby yield a brown oil (1.05 g). The oil was dissolved in ammonia-saturated methanol (30 mL), and the solution was stirred for 14 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (developer: chloroform:ammonia-saturated methanol=100:1→chloroform:ammonia-saturated methanol=20:1), to thereby yield 2-[4-(2-hydroxyethyl)piperazin-1-yl]-N-[2,4-bis(pyrrolidin-1-yl)-6-methyl-3-pyridyl]acetamide (911 mg, yield 95%) as a pale brown foamed substance.

後処理

  1. temperatureto reflux for 4 days
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was subjected to separation through silica gel column chromatography (developer: hexane:acetone=2:1)

出典と根拠

ORDレコード
ord-ed4037e8df894695980781f1861e04aa
出典データセット
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07560547B2

反応ノート

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