2-Aminopyridine → HCID 45257052, compound

HRID 520468Notes

Reaction equation

HRID 520468 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[C:7]([C:12](O)=[O:13])[CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[CH:3]1.CN(C(O[N:33]1N=N[C:35]2[CH:36]=[CH:37][CH:38]=[N:39][C:34]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.NC1C=CC=CN=1.C(N(C(C)C)CC)(C)C>CC(N(C)C)=O.O>[O:1]=[C:2]1[C:11]2[C:6](=[C:7]([C:12]([NH:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][N:39]=3)=[O:13])[CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:24])[F:23])[CH:16]=2)=[CH:3]1

Participants

7

Reactant 4

HCID 104392-AminopyridineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58552814HCID 58552814, compound

Product 1

HCID 45257052HCID 45257052, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 4-oxo-2-(3-(trifluoromethyl)phenyl)-1,4-dihydroquinoline-8-carboxylic acid 44 (250 mg, 0.750 mmol), HATU (570 mg, 1.5 mmol), 2-aminopyridine 21 (141 mg, 1.5 mmol) and diisopropylethylamine (392 μl, 2.25 mmol) in DMAC (5 mL) was heated at 75° C. for 16 h. The reaction mixture was poured in H2O (25 mL) and the resulting precipitate was collected by filtration. The crude residue was purified by MPLC Compound 401 (102 mg, 33% yield). MS (ESI) calc. for C22H14F3N3O2: 409.10. found: 410 [M+H].

Workup

  1. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-cdb069d3aa944052a67fdb7b163f0c5d
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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