Triethylamine → HCID 178476769, compound

HRID 1525231Notes

Reaction equation

HRID 1525231 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.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[CH3:47][P:48]([C:53]1[CH:58]=[CH:57][C:56]([CH:59]([NH2:66])[C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)=[CH:55][CH:54]=1)(=[O:52])[O:49][CH2:50][CH3:51]>CC#N>[OH:1][C:2]1[C:7]([C:8]([NH:66][CH:59]([C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=2)[C:56]2[CH:55]=[CH:54][C:53]([P:48]([CH3:47])(=[O:52])[O:49][CH2:50][CH3:51])=[CH:58][CH:57]=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 89462691Ethyl methyl(4-(amino(phenyl)methyl)phenyl)phosphinateHCID 178524762HCID 178524762, compound2×

Product 1

HCID 178476769HCID 178476769, 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, (206 mg, 1 mmol) in MeCN (20 ml) were added HATU (395 mg, 1.04 mmol), Et3N (105 mg, 1.04 mmol) and ethyl methyl(4-(amino(phenyl)methyl)phenyl)phosphinate, 2-d, (289 mg, 1 mmol). The resulting mixture was stirred at room temperature for 2 hours. Then it was filtered before diluted with saturated NH4Cl solution. The mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified on silica gel chromatography to provide the product, 8-3, (150 mg, 31%). 1H NMR (CD3OD, 300 MHz,): δ 8.65 (s, 1H), 8.57 (m, 1H), 7.91 (s, 1H), 7.76 (m, 2H), 7.52 (m, 2H), 7.34 (m, 5H), 6.64 (s, 1H), 6.36 (s, 1H), 3.85 (m, 2H), 1.67 (d, 3H), 1.25 (m, 3H).

Workup

  1. filtrationThen it was filtered
  2. additionbefore diluted with saturated NH4Cl solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified on silica gel chromatography
  7. customto provide the product, 8-3, (150 mg, 31%)

Sources & evidence

ORD record
ord-a995be2bd64743f7aedf6373569d757e
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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