4-Methylmorpholine → HCID 86656625, compound

HRID 882887Notes

Reaction equation

HRID 882887 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([OH:19])=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.[C:51]([O:55][C:56](=[O:77])[NH:57][C@H:58]([CH2:64][NH:65][C:66]([C:68]1[C:73]([NH2:74])=[N:72][C:71]([NH2:75])=[C:70]([Cl:76])[N:69]=1)=[O:67])[CH2:59][CH2:60][CH2:61][CH2:62][NH2:63])([CH3:54])([CH3:53])[CH3:52]>CN(C=O)C>[C:51]([O:55][C:56](=[O:77])[NH:57][C@H:58]([CH2:64][NH:65][C:66]([C:68]1[C:73]([NH2:74])=[N:72][C:71]([NH2:75])=[C:70]([Cl:76])[N:69]=1)=[O:67])[CH2:59][CH2:60][CH2:61][CH2:62][NH:63][C:17](=[O:19])[CH2:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)([CH3:54])([CH3:52])[CH3:53]

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 86651890HCID 86651890, compound2×

Product 1

HCID 86656625HCID 86656625, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(4-benzyloxyphenyl)propionic acid (0.19 g, 0.74 mmol) and HATU (0.29 g, 0.75 mmol) in DMF (10 mL) is added N-methylmorpholine (0.32 mL, 2.91 mmol) followed by ((S)-5-amino-1-{[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-pentyl)-carbamic acid tert-butyl ester (Intermediate B) (0.30 g, 0.75 mmol). The resulting mixture is stirred at RT for 16 h. The solvent is removed in vacuo and the residue is purified by column chromatography (basic alumina, 2% MeOH in DCM) to afford the title compound as yellow solid. [M-Boc+H]+ 540.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by column chromatography (basic alumina, 2% MeOH in DCM)

Sources & evidence

ORD record
ord-5f500cf220df4cfaa5ae1ca76bd2a33a
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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