4-Methylmorpholine → HCID 178468793, compound

HRID 412710Notes

Reaction equation

HRID 412710 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:18]=[CH:17][CH:16]=[CH:15][C:7]=1OCCCC(O)=O)=[O:5])[CH3:2].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.O.[OH:53][C:54]1C2N=NNC=2[CH:57]=[CH:56][CH:55]=1.CN1CCOCC1.[NH:70]1[C:78]2[CH2:77][CH2:76][NH:75][CH2:74][C:73]=2[N:72]=[C:71]1[CH:79]([C:81]1[NH:82][C:83]2[CH:89]=[C:88]([NH:90][C:91]([NH2:93])=[NH:92])[CH:87]=[CH:86][C:84]=2[N:85]=1)[CH3:80]>CN(C)C=O>[NH:90]([C:88]1[CH:87]=[CH:86][C:84]2[NH:85][C:81]([CH:79]([C:71]3[NH:70][C:78]4[CH2:77][CH2:76][N:75]([C:54](=[O:53])[CH2:55][CH2:56][CH2:57][C:7]5[CH:15]=[CH:16][CH:17]=[CH:18][C:6]=5[C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:74][C:73]=4[N:72]=3)[CH3:80])=[N:82][C:83]=2[CH:89]=1)[C:91]([NH2:93])=[NH:92]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 2724699PyBOPHCID 196227134-(2-Ethoxycarbonylphenoxy)butyric acidHCID 178437534HCID 178437534, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 178468793HCID 178468793, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture comprising 4-(2-ethoxycarbonylphenoxy)butyric acid (155 mg, 0.61 mmol), PyBOP (360 mg, 0.69 mmol), hydroxybenztriazole hydrate (87 mg, 0.64 mmol), N-methylmorpholine (0.16 mL, 0.92 mmol) and dimethylformamide (2.5 mL) was stirred at room temperature for 10 minutes and then N-{2-[1-(4,5,6,7-tetrahydroimidazo[4,5-c]pyridin-2-yl)ethyl]-3H-benzimidazol-5-yl }guanidine (203 mg, 0.63 mmol) was added. The mixture was stirred for 3 hours at room temperature and concentrated in vacuo. The residue was dissolved in 5% aqueous acetonitrile and the product purified by preparative reverse phase HPLC. The combined pure fractions were then lyophillized to provide ethyl 2-(4-{2-[1-(5-guanidino-1H-benzoimidazol-2-yl)ethyl]-1,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl}-4-oxobutyl)benzoate; LRMS (BioIon): calculated for C29H34N8O4: 558.6; Found: 559.3.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in 5% aqueous acetonitrile
  3. customthe product purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-6d44c144135949808e6034ec973e6411
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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