Isonicotinic Acid → HCID 68212825, compound

HRID 2089632Notes

Reaction equation

HRID 2089632 reaction equation
C(N(CC)CC)C.[N:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=1.CN(C(F)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:32][C:33](=[N:77][C:78](=[O:85])[C:79]1[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=1)[C:34]1[CH:39]=[CH:38][C:37]([NH:40][CH:41]([C:64]2[CH:69]=[C:68]([O:70][CH3:71])[CH:67]=[C:66]([O:72][CH2:73][CH2:74]O)[C:65]=2[F:76])[C:42]2[N:43]=[C:44]([O:53][CH2:54][O:55][C:56](=[O:63])[C:57]([CH3:62])([CH3:61])[CH2:58][O:59][CH3:60])[N:45]([C:47]3[N:52]=[CH:51][CH:50]=[CH:49][N:48]=3)[N:46]=2)=[CH:36][CH:35]=1>CN(C1C=CN=CC=1)C.ClCCl>[NH2:32][C:33](=[N:77][C:78](=[O:85])[C:79]1[CH:80]=[CH:81][CH:82]=[CH:83][CH:84]=1)[C:34]1[CH:39]=[CH:38][C:37]([NH:40][CH:41]([C:42]2[N:43]=[C:44]([O:53][CH2:54][O:55][C:56](=[O:63])[C:57]([CH3:62])([CH3:61])[CH2:58][O:59][CH3:60])[N:45]([C:47]3[N:52]=[CH:51][CH:50]=[CH:49][N:48]=3)[N:46]=2)[C:64]2[C:65]([F:76])=[C:66]([CH:67]=[C:68]([O:70][CH3:71])[CH:69]=2)[O:72][CH2:73][CH2:74][O:15][C:14]([C:11]2[CH:12]=[CH:13][N:8]=[CH:9][CH:10]=2)=[O:16])=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 5922Isonicotinic AcidHCID 8471TriethylamineHCID 2774761Tetramethylfluoroformamidinium hexafluorophosphateHCID 68212999HCID 68212999, compound

Product 1

HCID 68212825HCID 68212825, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Under nitrogen atmosphere, triethylamine (0.112 mL) was added under ice-cooling to a mixture of 4-pyridinecarboxylic acid [CAS No. 55-22-1] (19.6 mg), TFFH (42.4 mg), and dichloromethane (6 mL), and the resulting mixture was stirred for 1 hour. To the resulting mixture, 3-methoxy-2,2-dimethylpropionic acid 5-({4-[amino(benzoylimino)methyl]phenylamino}-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl)-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-ylox ymethyl ester (14.9 mg) and DMAP (0.27 mg) were added, and the resulting mixture was stirred overnight at room temperature. Under reduced pressure, the solvent in the mixture was distilled off. The residue obtained was purified by reverse phase high-performance liquid chromatography (mixed solvent of acetonitrile-water, containing 0.1% of acetic acid) to obtain the captioned compound (10.4 mg).

Workup

  1. distillationUnder reduced pressure, the solvent in the mixture was distilled off
  2. customThe residue obtained
  3. customwas purified by reverse phase high-performance liquid chromatography (mixed solvent of acetonitrile-water, containing 0.1% of acetic acid)

Sources & evidence

ORD record
ord-3b9b2a0ecf9744af9cd06ee2aa9827a3
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Reaction notes

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