4-Methylmorpholine → {3-[2-(4-Chloro-phenyl)-acetylamino]-propyl}-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium hexafluorophosphate

HRID 882895Notes

Reaction equation

HRID 882895 reaction equation
[Br-].[NH2:2][CH2:3][CH2:4][CH2:5][N+:6]([CH2:9][CH2:10][NH:11][C:12]([C:14]1[C:19]([NH2:20])=[N:18][C:17]([NH2:21])=[C:16]([Cl:22])[N:15]=1)=[O:13])([CH3:8])[CH3:7].[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31](O)=[O:32])=[CH:26][CH:25]=1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.[F:58][P-:59]([F:64])([F:63])([F:62])([F:61])[F:60]>CN(C=O)C>[F:58][P-:59]([F:64])([F:63])([F:62])([F:61])[F:60].[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]([NH:2][CH2:3][CH2:4][CH2:5][N+:6]([CH2:9][CH2:10][NH:11][C:12]([C:14]2[C:19]([NH2:20])=[N:18][C:17]([NH2:21])=[C:16]([Cl:22])[N:15]=2)=[O:13])([CH3:7])[CH3:8])=[O:32])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 15880(4-Chlorophenyl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86656637HCID 86656637, compound2×

Product 1

HCID 86656639{3-[2-(4-Chloro-phenyl)-acetylamino]-propyl}-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium hexafluorophosphate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (3-amino-propyl)-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide (Intermediate M) (0.25 g, 0.63 mmol), (4-chloro-phenyl)-acetic acid (0.11 g, 0.64 mmol), N-methylmorpholine (0.25 mL, 2.27 mmol) and HATU (0.24 g, 0.63 mmol) in anhydrous DMF (8 mL) is stirred under a nitrogen atmosphere at RT for 16 h. The reaction mixture is concentrated in vacuo and is purified by column chromatography (basic alumina, 0-4% MeOH in DCM) to afford the title compound. M+ 468. 1H NMR (400 MHz, DMSO-d6) δ 8.22 (1H, t), 8.14 (1H, t), 7.45 (2H, br), 7.32 (2H, d), 7.24 (2H, d), 7.08 (2H, br), 3.57-3.51 (2H, m), 3.43 (2H, s), 3.42-3.25 (4H, m), 3.12-3.03 (2H, m), 3.02 (6H, s), 1.86-1.78 (2H, m).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customis purified by column chromatography (basic alumina, 0-4% MeOH in DCM)

Sources & evidence

ORD record
ord-ab6713cf23ec4e24933b4d23bd75f142
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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