Glyoxylic Acid → HCID 118104167, compound

HRID 2207392Notes

Reaction equation

HRID 2207392 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([NH:15][C:16]3[N:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][N:17]=3)[CH:11]=[C:12]([CH3:14])[CH:13]=2)[CH:5]=[N:6][CH:7]=1.O=[CH:27][C:28]([OH:30])=[O:29].FC(F)(F)C(O)=O>CN(C=O)C>[CH3:14][C:12]1[CH:13]=[C:8]([C:4]2[CH:3]=[C:2]([NH:1][CH2:27][C:28]([OH:30])=[O:29])[CH:7]=[N:6][CH:5]=2)[CH:9]=[C:10]([NH:15][C:16]2[N:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][N:17]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 760Glyoxylic AcidHCID 6422Trifluoroacetic acidHCID 131735903HCID 131735903, compound

Product 1

HCID 118104167HCID 118104167, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-[3-(5-aminopyridin-3-yl)-5-methylphenyl]-4-(trifluoromethyl)pyrimidin-2-amine (20.0 mg, 0.058 mmol), oxoacetic acid (4.29 mg, 0.058 mmol) in DMF (0.579 mL, 0.1 M), and trifluoroacetic acid (8.92 μL, 0.116 mmol). was stirred for 1 hour at room temperature. Si-cyanoborohydride (123 mg, 0.116 mmol, 0.94 g/mmol) was added to the reaction mixture and stir for 12 hours at room temperature. The reaction mixture was filtered, concentrated in vacuo and the residue was purified by reverse phase liquid chromatography (5:95 to 95:5, acetonitrile:water+0.1% v/v formic acid) afforded N-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-3-yl]glycine as the formic acid salt. MS APCI calc'd for C19H17F3N5O2 [M+H]+ 404. found 404. 1H NMR (600 MHz, DMSO-d6) δ 10.24 (s, 1H), 8.82 (d, J=4.9 Hz, 1H), 8.02 (d, J=1.8 Hz, 1H), 7.96 (d, J=2.6 Hz, 1H), 7.89 (s, 1H), 7.53 (s, 1H), 7.26 (d, J=4.9 Hz, 1H), 7.11 (s, 1H), 7.05 (s, 2H), 3.91 (s, 2H), 2.34 (s, 3H).

Workup

  1. stirringstir for 12 hours at room temperature
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by reverse phase liquid chromatography (5:95 to 95:5, acetonitrile

Sources & evidence

ORD record
ord-3d080e21030a4b62947f3ec4e0ea7abd
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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