Triethylamine → HCID 178476965, compound

HRID 1525219Notes

Reaction equation

HRID 1525219 reaction equation
[OH:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[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.[NH2:48][CH:49]([C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)[C:50]1[CH:51]=[CH:52][C:53]([P:56](=[O:63])([O:60][CH2:61][CH3:62])[O:57][CH2:58][CH3:59])=[N:54][CH:55]=1>C(OCC)(=O)C>[OH:1][C:2]1[C:7]([C:8]([NH:48][CH:49]([C:64]2[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=2)[C:50]2[CH:51]=[CH:52][C:53]([P:56](=[O:63])([O:60][CH2:61][CH3:62])[O:57][CH2:58][CH3:59])=[N:54][CH:55]=2)=[O:10])=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[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 131733139Diethyl {5-[amino(phenyl)methyl]pyridin-2-yl}phosphonateHCID 178524750HCID 178524750, compound

Product 1

HCID 178476965HCID 178476965, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-hydroxy-2-(pyridin-2-yl)pyrimidine-5-carboxylic acid, 1-1-h, (1 g, 4.6 mmol) in ethyl acetate (20 ml) was added HATU (1.75 g, 4.6 mmol), Et3N (465 mg, 4.6 mmol) and diethyl {5-[amino(phenyl)methyl]pyridin-2-yl}phosphonate (4-g) (1.47 g, 4.6 mmol). The resulting mixture was stirred at room temperature for 2 hour. 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, 4-1, (360 mg, 15%). 1H NMR (CD3OD, 300 MHz,): δ 10.56 (m, 1H), 8.66 (m, 3H), 8.37 (m, 1H), 7.83 (m, 3H), 7.52 (m, 1H), 7.23 (m, 5H), 6.33 (m, 1H), 4.09 (m, 4H), 1.30 (m, 6H).

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, 4-1, (360 mg, 15%)

Sources & evidence

ORD record
ord-cf7c5c835414429a89055b348a02dace
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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