4-Methylmorpholine → HCID 178508754, compound

HRID 1665131Notes

Reaction equation

HRID 1665131 reaction equation
[NH2:1][C:2]1[C:3]([C:10](/[N:12]=[C:13]2\[NH:14][CH2:15][C:16]3([CH2:23][CH:22]4[NH:24][CH:19]([CH2:20][CH2:21]4)[CH2:18]3)[NH:17]\2)=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:49]([O:56][C:57]1[CH:62]=[CH:61][C:60]([CH2:63][CH2:64][C:65](O)=[O:66])=[CH:59][CH:58]=1)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.CN1CCOCC1>CN(C=O)C>[NH2:1][C:2]1[C:3]([C:10](/[N:12]=[C:13]2\[NH:14][CH2:15][C:16]3([CH2:23][CH:22]4[N:24]([C:65](=[O:66])[CH2:64][CH2:63][C:60]5[CH:61]=[CH:62][C:57]([O:56][CH2:49][C:50]6[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=6)=[CH:58][CH:59]=5)[CH:19]([CH2:20][CH2:21]4)[CH2:18]3)[NH:17]\2)=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 5613723-(4-Benzyloxyphenyl)propionic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178508756HCID 178508756, compound

Product 1

HCID 178508754HCID 178508754, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(E)-3,5-diamino-6-chloro-N-(8-azaspiro[bicyclo[3.2.1]octane-3,4′-imidazolidine]-2′-ylidene)pyrazine-2-carboxamide (prepared as described for Ex. 252) (280 mg, 0.798 mmol) is dissolved in DMF (8 ml) along with HATU (303 mg, 0.798 mmol) and 3-(4-benzyloxy-phenyl)-propionic acid (205 mg, 0.798 mmol). N-Methyl morpholine (0.263 ml, 2.394 mmol) is added and the solution stirred at room temperature for 6 hours. The mixture is then concentrated in vacuo. EtOAc (100 ml) is added and the solution washed with water (100 ml). The organic phase is dried (MgSO4) and concentrated. The residue is dissolved in MeOH (20 ml) and dry loaded onto silica (5 g). Purification by flash chromatography (SiO2, DCM/MeOH) gives the title compound as a tan solid; [M+H]+ 589.20, 591.19 for Cl isotopes.

Workup

  1. concentrationThe mixture is then concentrated in vacuo
  2. additionEtOAc (100 ml) is added
  3. washthe solution washed with water (100 ml)
  4. dry with materialThe organic phase is dried (MgSO4)
  5. concentrationconcentrated
  6. dissolutionThe residue is dissolved in MeOH (20 ml)
  7. customdry
  8. customPurification by flash chromatography (SiO2, DCM/MeOH)

Sources & evidence

ORD record
ord-4e8e9cdf96cf49978157b282300a7a0d
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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