Isonicotinic Acid → HCID 44468933, compound

HRID 929506Notes

Reaction equation

HRID 929506 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)=[O:9])[CH2:3][CH2:2]1.[C:22](O)(=[O:29])[C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1>>[C:22]([N:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:19])([F:20])[F:21])=[CH:13][CH:12]=2)=[O:9])[CH2:3][CH2:2]1)(=[O:29])[C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 5922Isonicotinic AcidHCID 49780164HCID 49780164, compound

Product 1

HCID 44468933HCID 44468933, compound

Procedure

Intermediate 42 (152 mg, 0.5 mmol) was reacted with isonicotinic acid by Method E. Flash chromatography eluted with 9:1 DCM:MeOH afforded compound 47 (204 mg, 100%) as a white solid: Mp 210-212° C. 1H NMR (500 MHz, DMSO-d6) δ 8.67 (d, J=6 Hz, 2H), 8.59 (s, 1H), 7.47 (d, J=9 Hz, 2H), 7.38 (d, J=6 Hz, 2H), 7.22 (d, J=9 Hz, 2H), 6.25 (d, J=8 Hz, 1H), 4.30 (d, J=12 Hz, 1H), 3.76 (s, 1H), 3.41 (d, J=12 Hz, 1H), 3.16 (t, J=12 Hz, 1H), 3.05 (t, J=12 Hz, 1H), 1.97-1.88 (m, 1H), 1.84-1.75 (m, 1H), 1.47-1.29 (m, 2H). Purity 92%. HRMS calculated for C19H19F3N4O3−H+ 407.1331. found (ESI(−), [M−H]) 407.1316.

Workup

  1. washFlash chromatography eluted with 9:1 DCM

Sources & evidence

ORD record
ord-9b36006ed0254f9ea2c2d86126ef97a3
Source dataset
uspto-grants-2016_03
Patent number
US09296693B2

Reaction notes

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