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 882893Notes

Reaction equation

HRID 882893 reaction equation
[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

Participants

4

Reactant 2

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

Product 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

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-bfacbfbd3feb48b7846b9390be659d88
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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