Triethylamine → HCID 178476759, compound

HRID 1525279Notes

Reaction equation

HRID 1525279 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]([C:62]1[CH:67]=[CH:66][CH:65]=[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>CC#N>[OH:1][C:2]1[C:7]([C:8]([NH:48][C@H:49]([C:62]2[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=2)[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)=[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 89462726Ethyl 4-((R)-amino(phenyl)methyl)phenyl(methyl)phosphinate hydrochloride2×HCID 178524762HCID 178524762, compound2×

Product 1

HCID 178476759HCID 178476759, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylic acid, 8-b, (2.5 g, 12.11 mmol) and Et3N (4.3 mg, 43 mmol) in MeCN (50 ml) was added HATU (4.83 mg, 12.72 mmol). The mixture was stirred for 5 min at room temperature and then ethyl 4-((R)-amino(phenyl)methyl)phenyl(methyl)phosphinate hydrochloride, 23-c, (3.5 g, 12.1 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=2/1) to provide the product, 23-d, (4 g, 69%).

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=2/1)
  7. customto provide the product, 23-d, (4 g, 69%)

Sources & evidence

ORD record
ord-6658fe1b281c4b36981be8816e16d557
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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