Picolinic acid → HCID 44201107, compound

HRID 2061184Notes

Reaction equation

HRID 2061184 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:43]([C:45]1[CH:54]=[C:53]2[C:48]([CH:49]=[C:50]([C:57]3[CH:58]=[C:59]([NH:64]/[C:65](/[NH2:68])=[N:66]/O)[CH:60]=[CH:61][C:62]=3[CH3:63])[C:51](=[O:56])[N:52]2[CH3:55])=[CH:47][N:46]=1)[CH3:44]>CN(C=O)C>[CH2:43]([C:45]1[CH:54]=[C:53]2[C:48]([CH:49]=[C:50]([C:57]3[CH:58]=[C:59]([NH:64][C:65]4[N:66]=[C:7]([C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=5)[O:9][N:68]=4)[CH:60]=[CH:61][C:62]=3[CH3:63])[C:51](=[O:56])[N:52]2[CH3:55])=[CH:47][N:46]=1)[CH3:44]

Participants

6

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 178435387HCID 178435387, compound2×

Product 1

HCID 44201107HCID 44201107, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of picolinic acid (10 mg, 0.09 mmol) in DMF (1 mL) were added DIPEA (16 μL, 0.09 mmol) and HATU (33 mg, 0.09 mmol). After stirring at rt for 15 min, 17a (30 mg, 0.09 mmol) was added as a solution in DMF (0.5 mL). The reaction was stirred at rt until complete consumption of 17a was determined by LC/MS and then heated at 100° C. for 1 h. Subsequently the reaction was cooled to rt, filtered and purified by preparative LC/MS to give 7-ethyl-1-methyl-3-(2-methyl-5-(5-(pyridin-2-yl)-1,2,4-oxadiazol-3-ylamino)phenyl)-1,6-naphthyridin-2(1H)-one (A105). 1H NMR (400 MHz, d6-DMSO) δ 10.13 (s, 1H), 9.09 (s, 1H), 8.81 (s, 1H), 8.18 (d. J=8 Hz, 1H), 8.10 (m, 2H), 7.75 (s, 1H), 7.71 (m, 1H), 7.47 (d, J=8 Hz, 1H), 7.41 (s, 1H), 7.28 (d, J=8 Hz, 1H), 3.72 (s, 3H), 3.01 (q, J=7.6 Hz, 2H), 2.10 (s, 3H), 1.36 (t, J=7.6 Hz, 3H). MS m/z 439.3 (M+1).

Workup

  1. temperatureheated at 100° C. for 1 h
  2. temperatureSubsequently the reaction was cooled to rt
  3. filtrationfiltered
  4. custompurified by preparative LC/MS

Sources & evidence

ORD record
ord-f7c2dcab95f94962be36a95155480e87
Source dataset
uspto-grants-2012_10
Patent number
US08278452B2

Reaction notes

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