Triethylamine → HCID 178476767, compound

HRID 1525305Notes

Reaction equation

HRID 1525305 reaction equation
[F:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[N:12]=[C:11]([OH:13])[C:10]([C:14]([OH:16])=O)=[CH:9][N:8]=2)[CH:6]=1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:48][C@H:49]([C:62]1[CH:67]=[CH:66][C:65]([F:68])=[CH:64][CH: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.Cl.N[C@H](C1C=CC(F)=CC=1)C1C=CC(P(C)(=O)OCC)=CC=1>CC#N>[F:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[N:12]=[C:11]([OH:13])[C:10]([C:14]([NH:48][C@H:49]([C:62]3[CH:63]=[CH:64][C:65]([F:68])=[CH:66][CH:67]=3)[C:50]3[CH:55]=[CH:54][C:53]([P:56]([CH3:61])(=[O:60])[O:57][CH2:58][CH3:59])=[CH:52][CH:51]=3)=[O:16])=[CH:9][N:8]=2)[CH:6]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89462169ethyl 4-((R)-amino(4-fluoro phenyl)methyl)phenyl(methyl)phosphinateHCID 117702271Ethyl 4-((R)-amino(4-fluorophenyl)methyl)phenyl(methyl)phosphinate hydrochlorideHCID 178524763HCID 178524763, compound

Product 1

HCID 178476767HCID 178476767, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 28-g (2.8 g, 12 mmol) and Et3N (3.5 g, 34 mmol) in MeCN (30 ml) was added HATU (4.8 g, 12 mmol). The mixture was stirred for 5 min at room temperature and then ethyl 4-((R)-amino(4-fluoro phenyl)methyl)phenyl(methyl)phosphinate, 18-e, (3.5 g, 11 mmol) was added. The resulting mixture was stirred at room temperature for 1 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 (petroleum ether:ethyl acetate=1/1) to provide the product, 29-a, (1 g, 15.7%).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 1 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 (petroleum ether:ethyl acetate=1/1)

Sources & evidence

ORD record
ord-6f7888c034464ccfad640a0213454f74
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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