Picolinic acid → HCID 44554276, compound

HRID 2359442Notes

Reaction equation

HRID 2359442 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[CH:12][C:13]3[N:14]=[CH:15][N:16]=[C:17]([NH2:20])[C:18]=3[N:19]=2)[CH:7]=[CH:8][CH:9]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[C:53](O)=[O:54].CCN(C(C)C)C(C)C>CN(C=O)C.O>[F:22][C:2]([F:1])([F:21])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[CH:12][C:13]3[N:14]=[CH:15][N:16]=[C:17]([NH:20][C:53](=[O:54])[C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][N:47]=4)[C:18]=3[N:19]=2)[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58154519HCID 58154519, compound

Product 1

HCID 44554276HCID 44554276, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(3-(trifluoromethoxy)phenyl)pyrido[3,2-d]pyrimidin-4-amine (50 mg, 163 mmol) in DMF (1 mL) was added HATU (124 mg, 330 mmol), pyridine-2-carboxylic acid (20 mg, 163 mmol) and DIPEA (0.07 mL, 330 mmol). The mixture was stirred at room temperature for 18 hours. The reaction mixture was treated with water and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), concentrated to dryness and the crude product was purified by prep-TLC (10% Methanol in CH2Cl2) to afford N-(6-(3-(trifluoromethoxy)phenyl)pyrido[3,2-d]pyrimidin-4-yl)picolinamide as a yellow solid (57 mg, 85% yield). MS (ESI) calcd for C20H12F3N5O2 (m/z): 411.09. found: 412 [M+1].

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to dryness
  5. customthe crude product was purified by prep-TLC (10% Methanol in CH2Cl2)

Sources & evidence

ORD record
ord-7e6e2715a7234b9f9e674f5295a91abb
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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