3,5-Diamino-6-chloro-N-[2-(dimethylamino)ethyl]-2-pyrazinecarboxamide → {2-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-[3-(4-{3-[4-((S)-2,3-dihydroxy-propoxy)-phenyl]-propoxy}-phenyl)-propyl]-dimethyl-ammonium bromide

HRID 882893ノート

反応式

HRID 882893 の反応式
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:13]([NH2:14])=[N:12][C:11]([NH2:15])=[C:10]([Cl:16])[N:9]=1)=[O:7].[Br:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:43]=[CH:42][C:25]([O:26][CH2:27][CH2:28][CH2:29][C:30]2[CH:41]=[CH:40][C:33]([O:34][CH2:35][C@@H:36]([OH:39])[CH2:37][OH:38])=[CH:32][CH:31]=2)=[CH:24][CH:23]=1>CC(=O)CC>[Br-:18].[NH2:14][C:13]1[C:8]([C:6]([NH:5][CH2:4][CH2:3][N+:2]([CH2:19][CH2:20][CH2:21][C:22]2[CH:43]=[CH:42][C:25]([O:26][CH2:27][CH2:28][CH2:29][C:30]3[CH:31]=[CH:32][C:33]([O:34][CH2:35][C@@H:36]([OH:39])[CH2:37][OH:38])=[CH:40][CH:41]=3)=[CH:24][CH:23]=2)([CH3:17])[CH3:1])=[O:7])=[N:9][C:10]([Cl:16])=[C:11]([NH2:15])[N:12]=1

参加物

4

反応物 2

HCID 151481303,5-Diamino-6-chloro-N-[2-(dimethylamino)ethyl]-2-pyrazinecarboxamide2 回HCID 67028182(S)-3-(4-{3-[4-(3-bromo-propyl)-phenoxy]-propyl}-phenoxy)-propane-1,2-diol2 回

生成物 1

HCID 86656635{2-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-[3-(4-{3-[4-((S)-2,3-dihydroxy-propoxy)-phenyl]-propoxy}-phenyl)-propyl]-dimethyl-ammonium bromide

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid (2-dimethylamino-ethyl)-amide (Intermediate H) (0.65 g, 2.52 mmol) and (S)-3-(4-{3-[4-(3-bromo-propyl)-phenoxy]-propyl}-phenoxy)-propane-1,2-diol (Intermediate J) (1.60 g, 3.78 mmol) in butan-2-one (25 mL) is heated at reflux overnight during which time precipitation of white solid is observed. The reaction mixture is filtered to collect the product, washed with warm acetone and dried under vacuum to afford the title compound. M+ 601. 1H NMR (400 MHz, DMSO-d6) δ 8.29 (1H, t), 7.30 (1H, br), 7.12 (2H, d), 7.11 (2H, br), 7.07 (2H, d), 6.95 (1H, br), 6.84 (2H, d), 6.82 (2H, d), 4.89 (1H, d), 4.63 (1H, t), 3.94 (1H, dd), 3.89 (2H, t), 3.81 (1H, dd), 3.77 (1H, m), 3.59 (2H, m), 3.43 (2H, m), 3.42 (2H, m), 3.34 (2H, m), 3.08 (6H, s), 2.66 (2H, m), 2.47 (2H, m), 1.96 (2H, m), 1.93 (2H, m).

後処理

  1. temperatureat reflux overnight during which time precipitation of white solid
  2. filtrationThe reaction mixture is filtered
  3. customto collect the product
  4. washwashed with warm acetone
  5. customdried under vacuum

出典と根拠

ORDレコード
ord-bfacbfbd3feb48b7846b9390be659d88
出典データセット
uspto-grants-2012_08
特許番号
US08236808B2

反応ノート

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