HCID 69046398, compound → 3-amino-N-(4-((S)-3-aminopiperidin-1-yl)pyridin-3-yl)-6-(2,6-difluoro-3-hydroxyphenyl)-5-fluoropicolinamide

HRID 69978Notes

Reaction equation

HRID 69978 reaction equation
[NH2:1][C:2]1[C:3]([C:25]([NH:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][C:33]=2[N:34]2[CH2:39][CH2:38][CH2:37][C@H:36]([NH2:40])[CH2:35]2)=[O:26])=[N:4][C:5]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[C:11]([O:16]CC3C=CC=CC=3)[C:10]=2[F:24])=[C:6]([F:8])[CH:7]=1>CO.[Pd]>[NH2:1][C:2]1[C:3]([C:25]([NH:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][C:33]=2[N:34]2[CH2:39][CH2:38][CH2:37][C@H:36]([NH2:40])[CH2:35]2)=[O:26])=[N:4][C:5]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[C:11]([OH:16])[C:10]=2[F:24])=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 1

HCID 69046398HCID 69046398, compound

Product 1

HCID 690474413-amino-N-(4-((S)-3-aminopiperidin-1-yl)pyridin-3-yl)-6-(2,6-difluoro-3-hydroxyphenyl)-5-fluoropicolinamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Method 2 of Example 49 was followed using 3-amino-N-(4-((S)-3-aminopiperidin-1-yl)pyridin-3-yl)-6-(3-(benzyloxy)-2,6-difluorophenyl)-5-fluoropicolinamide with 20 wt % Pd/C in methanol (0.1 M solution). The Boc protected product was purified by preparative HPLC. After volatile materials were removed, the crude material was stirred in 30% TFA in dichloromethane. After volatile materials were removed in vacuo, 3-amino-N-(4-((S)-3-aminopiperidin-1-yl)pyridin-3-yl)-6-(2,6-difluoro-3-hydroxyphenyl)-5-fluoropicolinamide was obtained by preparative HPLC. LCMS (m/z): 459.2 (MH+); LC Rt=2.10 min.

Workup

  1. customThe Boc protected product was purified by preparative HPLC
  2. customAfter volatile materials were removed
  3. customAfter volatile materials were removed in vacuo

Sources & evidence

ORD record
ord-fe0e47b5fef745d2b833bc1b4dfba5f8
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

Loading…