Triethylamine → HCID 178460699, compound

HRID 1525247Notes

Reaction equation

HRID 1525247 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.[NH2:47][CH:48]([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[C:49]1[CH:54]=[CH:53][C:52]([P:55]([CH2:60][CH2:61][CH3:62])(=[O:59])[O:56][CH2:57][CH3:58])=[CH:51][CH:50]=1>CC#N>[OH:1][C:2]1[C:7]([C:8]([NH:47][CH:48]([C:63]2[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=2)[C:49]2[CH:50]=[CH:51][C:52]([P:55]([CH2:60][CH2:61][CH3:62])(=[O:59])[O:56][CH2:57][CH3:58])=[CH:53][CH:54]=2)=[O:10])=[CH:6][N:5]=[C:4]([N:11]2[CH:15]=[CH:14][CH:13]=[N:12]2)[N:3]=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 89462676Ethyl 4-(amino(phenyl)methyl)phenyl(propyl)phosphinate2×HCID 178524762HCID 178524762, compound

Product 1

HCID 178460699HCID 178460699, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylic acid (8-b, 526 mg, 2.56 mmol) in MeCN (10 ml) was added Et3N (645 mg, 6.39 mmol), then added HATU (1068 mg, 2.81 mmol). After 5 mins, ethyl 4-(amino(phenyl)methyl)phenyl(propyl)phosphinate, 16-e, (810 mg, 2.56 mmol) was added and the resulting mixture was stirred at rt for 2 hours. The mixture was then evaporated and the residue was diluted with ethyl acetate followed by washing with brine. The organic layer was dried and concentrated under vacuo to give the title compound, 16-f, (crude product, 2.1 g).

Workup

  1. customThe mixture was then evaporated
  2. additionthe residue was diluted with ethyl acetate
  3. washby washing with brine
  4. customThe organic layer was dried
  5. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-6f07febe0ec04d3c90e10e7a4b4278ce
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

Loading…