Triethylamine → HCID 178476760, compound

HRID 1525298Notes

Reaction equation

HRID 1525298 reaction equation
[OH:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([N:11]2[CH:15]=[CH:14][CH:13]=[N:12]2)[N:3]=1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:48][C@@H:49]([CH:62]1[CH2:67][CH2:66][CH2:65][CH2:64][CH2:63]1)[C:50]1[CH:55]=[CH:54][C:53]([P:56]([CH3:61])(=[O:60])[O:57][CH2:58][CH3:59])=[CH:52][CH:51]=1>CN(C=O)C>[CH:62]1([C@H:49]([NH:48][C:8]([C:7]2[C:2]([OH:1])=[N:3][C:4]([N:11]3[CH:15]=[CH:14][CH:13]=[N:12]3)=[N:5][CH:6]=2)=[O:10])[C:50]2[CH:51]=[CH:52][C:53]([P:56]([CH3:61])(=[O:60])[O:57][CH2:58][CH3:59])=[CH:54][CH:55]=2)[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89462086HCID 89462086, compoundHCID 178524762HCID 178524762, compound

Product 1

HCID 178476760HCID 178476760, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 8-b (2.6 g, 12.6 mmol) and Et3N (3.8 g, 37.8 mmol) in DMF (50 mL) was added HATU (5.8 g, 15.2 mmol). The mixture was stirred for 5 min at room temperature and then ethyl 4-((S)-amino(cyclohexyl)methyl)phenyl(methyl)phosphinate hydrochloride, 27-d, (4.2 g, 12.6 mmol) was added. The resulting mixture was stirred at room temperature for 15 hour. The mixture was then concentrated under vacuum and the residue was taken into ethyl acetate followed by washing with 1N HCl. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified on silica gel chromatography (ethyl acetate:MeOH=10/1) to provide the product, 27-e, (3.3 g, 54.1%).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 15 hour
  2. concentrationThe mixture was then concentrated under vacuum
  3. washby washing with 1N HCl
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified on silica gel chromatography (ethyl acetate:MeOH=10/1)

Sources & evidence

ORD record
ord-26fdff12aa5b453482e7121f460f37fd
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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