Isonicotinic Acid → HCID 57893559, compound

HRID 1821851Notes

Reaction equation

HRID 1821851 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[C:10]1([CH:16]([NH2:26])[C:17]2[NH:25][C:20]3=[CH:21][N:22]=[CH:23][CH:24]=[C:19]3[CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:10]1([CH:16]([C:17]2[NH:25][C:20]3=[CH:21][N:22]=[CH:23][CH:24]=[C:19]3[CH:18]=2)[NH:26][C:1](=[O:9])[C:2]2[CH:3]=[CH:4][N:5]=[CH:6][CH:7]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 5922Isonicotinic AcidHCID 57893560HCID 57893560, compound

Product 1

HCID 57893559HCID 57893559, compoundYield 44%

Procedure

Using the procedure described for Example 43 with isonicotinic acid at room temperature, the reaction was stopped once 1-phenyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)methylamine was consumed as judged by TLC analysis. Upon addition of water a solid precipitated. The solid was collected by filtration and dried to provide N-[phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methyl]isonicotinamide (58 mg, 44%) as an off-white solid: mp 182-192° C.; 1H NMR (300 MHz, CD3OD) δ6.34 (1H, s), 6.67 (1H, s), 7.30-7.55 (7H, m), 7.84-7.87 (2H, m), 8.04 (1H, d, J=5.7 Hz), 8.63 (1H, s), 8.69-8.71 (1H, m); ESI MS m/z 329 [C20H16N4O+H]+; HPLC (Method A) >99% (AUC) tR=14.1 min.

Workup

  1. customwas consumed
  2. additionUpon addition of water a solid
  3. customprecipitated
  4. filtrationThe solid was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-acbea33e2d55492c892958597f6d515d
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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