Picolinic acid → HCID 57893521, compound

HRID 1821852Notes

Reaction equation

HRID 1821852 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.[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:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:9])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 1018Picolinic acidHCID 57893560HCID 57893560, compound

Product 1

HCID 57893521HCID 57893521, compoundYield 6%

Procedure

Using the procedure described for Example 43 with picolinic 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. Purification by Biotage chromatography provided N-[phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methyl]-2-pyridinecarboxamide (8 mg, 6%) as an off-white solid: mp 102-110° C.; 1H NMR (300 MHz, CD3OD) δ 6.42 (1H, s), 6.64 (1H, s), 7.36-7.62 (7H, m), 7.98-8.03 (2H, m), 8.13-8.16 (1H, m), 8.59 (1H, s), 8.63-8.67 (1H, m); ESI MS m/z 329 [C20H16N4O+H]+; HPLC (Method A) >99% (AUC) tR=15.8 min.

Workup

  1. customwas consumed
  2. customPurification by Biotage chromatography

Sources & evidence

ORD record
ord-a7f708c64d7a4167aebe4ecaf02e6e6d
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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