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

HRID 882896Notes

Reaction equation

HRID 882896 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[Br-:50].[NH2:51][CH2:52][CH2:53][CH2:54][CH2:55][N+:56]([CH2:59][CH2:60][NH:61][C:62]([C:64]1[C:69]([NH2:70])=[N:68][C:67]([NH2:71])=[C:66]([Cl:72])[N:65]=1)=[O:63])([CH3:58])[CH3:57]>CN(C=O)C>[Br-:50].[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([NH:51][CH2:52][CH2:53][CH2:54][CH2:55][N+:56]([CH2:59][CH2:60][NH:61][C:62]([C:64]2[C:69]([NH2:70])=[N:68][C:67]([NH2:71])=[C:66]([Cl:72])[N:65]=2)=[O:63])([CH3:58])[CH3:57])=[O:18])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 810334-Benzyloxyphenylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86656640(4-Amino-butyl)-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide2×

Product 1

HCID 57402003{4-[2-(4-Benzyloxy-phenyl)-acetylamino]-butyl}-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-Benzyloxyphenyl acetic acid (0.013 g, 0.30 mmol) in DMF (1.5 mL) is added HATU (0.12 g, 0.3 mmol), N-methylmorpholine (0.13 mL, 1.2 mmol) and (4-amino-butyl)-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide (Intermediate N) (0.1 g, 0.30 mmol). The solution is stirred at RT for 2 h. The solvent is removed in vacuo and the residue is purified by reverse phase chromatography (Isolute™ C18, 0-100% acetonitrile in water with 0.1% TFA) to yield the title compound. M+ 535. 1H NMR (400 MHz, DMSO-d6) δ 8.25 (1H, t), 8.05 (1H, t), 7.25 (2H, br), 7.42-7.32 (5H, m), 7.17 (2H, d), 7.09 (2H, br), 6.92 (2H, d), 5.06 (2H, s), 3.61-3.53 (2H, m), 3.39-3.33 (4H, m), 3.32 (2H, s), 3.10-3.03 (2H, m), 3.02 (6H, s), 1.61-1.49 (2H, m), 1.44-1.33 (2H, m).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by reverse phase chromatography (Isolute™ C18, 0-100% acetonitrile in water with 0.1% TFA)

Sources & evidence

ORD record
ord-9e07498d4d6d427181043782ccea1734
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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