Triethylamine → HCID 178476761, compound

HRID 1525292Notes

Reaction equation

HRID 1525292 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]([CH:62]1[CH2:67][CH2:66][CH2:65][CH2:64][CH2:63]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>CN(C=O)C>[CH:62]1([C@@H:49]([NH:48][C:8]([C:7]2[C:2]([OH:1])=[N:3][C:4]([N:11]3[CH:15]=[CH:14][CH:13]=[N:12]3)=[N:5][CH:6]=2)=[O:10])[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)[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67]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 89462912HCID 89462912, compoundHCID 178524762HCID 178524762, compound2×

Product 1

HCID 178476761HCID 178476761, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylic acid, 8-b, (1.187 g, 5.76 mmol) and Et3N (1.75 mg, 17.3 mmol) in DMF (15 mL) was added HATU (2.62 mg, 6.9 mmol). The mixture was stirred for 5 min at room temperature and then compound 26-e (1.7 g, 5.76 mmol) was added. The resulting mixture was stirred at room temperature for 15 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 (ethyl acetate:MeOH=5/1) to provide the product, 26-f, (1.05 g, 49%).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 15 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 (ethyl acetate:MeOH=5/1)

Sources & evidence

ORD record
ord-d8da131e5670444b9cf83ac143e93cf4
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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