Triethylamine → HCID 178476770, compound

HRID 1525250Notes

Reaction equation

HRID 1525250 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][CH:49]([C:62]1[CH:67]=[CH:66][C:65]([F:68])=[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>[F:68][C:65]1[CH:64]=[CH:63][C:62]([CH: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:55]=[CH:54][C:53]([P:56]([CH3:61])(=[O:60])[O:57][CH2:58][CH3:59])=[CH:52][CH:51]=2)=[CH:67][CH:66]=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 89463291HCID 89463291, compoundHCID 178524762HCID 178524762, compound2×

Product 1

HCID 178476770HCID 178476770, compoundYield 27%

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, (275 mg, 1.33 mmol) and Et3N (404 mg, 4 mmol) in MeCN (6 ml) was added HATU (558 mg, 1.47 mmol). The mixture was stirred for 5 min at room temperature and then compound 17-e (450 mg, 1.47 mmol) was added. The resulting mixture was stirred at room temperature for 1 hour. Then the mixture was 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 (CH2Cl2:CH3OH=50/1) to provide the product, 17-f, (180 mg, 27%).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 1 hour
  2. concentrationThen the mixture was 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 (CH2Cl2:CH3OH=50/1)

Sources & evidence

ORD record
ord-e86f35324d944146a2b686ffd1f8b612
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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