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 882893노트

반응식

HRID 882893 반응식
[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

참가 물질

4

반응물 2

HCID 151481303,5-Diamino-6-chloro-N-[2-(dimethylamino)ethyl]-2-pyrazinecarboxamide2회HCID 67028182(S)-3-(4-{3-[4-(3-bromo-propyl)-phenoxy]-propyl}-phenoxy)-propane-1,2-diol2회

생성물 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

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bfacbfbd3feb48b7846b9390be659d88
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236808B2

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