4-Pyridineacetic acid → HCID 60207819, compound

HRID 910262Notes

Reaction equation

HRID 910262 reaction equation
[CH2:1]([C:5]1[N:9]([C:10]2[N:15]=[C:14]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[C:13]([CH3:21])=[CH:12][N:11]=2)[N:8]=[CH:7][C:6]=1[NH2:22])[CH2:2][CH2:3][CH3:4].[N:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](O)=[O:31])=[CH:25][CH:24]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.C([O-])(O)=O.[Na+]>[CH2:1]([C:5]1[N:9]([C:10]2[N:15]=[C:14]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[C:13]([CH3:21])=[CH:12][N:11]=2)[N:8]=[CH:7][C:6]=1[NH:22][C:30](=[O:31])[CH2:29][C:26]1[CH:27]=[CH:28][N:23]=[CH:24][CH:25]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 342284-Pyridineacetic acidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 60207822HCID 60207822, compound

Product 1

HCID 60207819HCID 60207819, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 5-butyl-1-(5-methyl-4-(thiophen-2-yl)pyrimidin-2-yl)-1H-pyrazol-4-amine (51 mg, 0.163 mmol, 1.0 equiv) and 2-(pyridin-4-yl)acetic acid (56 mg, 0.323 mmol, 2.0 equiv) in DMF (1 mL) was added HBTU (51 mg, 0.179 mmol, 1.1 equiv) and DIEA (91 μL, 0.520 mmol, 3.2 equiv) and heated to 40° C. and let stir for 15 h. The reaction was diluted with saturated NaHCO3 solution (15 mL) and extracted with a solution of 30% IPA in CHCl3 (3×20 mL). The organic layer dried (sodium sulfate), concentrated, and the residue was purified by silica gel flash column chromatography (10% methanol in dichloromethane) afford 35 (45 mg, 64% yield) as an off-white amorphous solid. 1H NMR (400 MHz, CD3OD) δ 8.65 (s 1H), 8.51 (d, J=5.6 Hz, 2H), 7.91 (d, J=4.4 Hz, 2H), 7.75 (d, J=5.2 Hz, 1H), 7.48 (d, J=5.6 Hz, 2H), 7.27 (t, J=4.0 Hz, 1H), 3.83 (s, 2H), 3.22 (t, J=7.6 Hz, 2H), 2.60 (s, 3H), 1.48 (quint, J=7.6 Hz, 2H), 1.25 (sex, J=7.2 Hz, 2H), 0.77 (t, J=7.2 Hz, 3H). LCMS (ES+) m/z 433 (M+1).

Workup

  1. extractionextracted with a solution of 30% IPA in CHCl3 (3×20 mL)
  2. dry with materialThe organic layer dried (sodium sulfate)
  3. concentrationconcentrated
  4. customthe residue was purified by silica gel flash column chromatography (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-7c9a9833d85e43d9be32e83db7da0e78
Source dataset
uspto-grants-2011_09
Patent number
US08022061B2

Reaction notes

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