3-Amino-6-bromo-5-fluoropicolinic acid → (S)-tert-butyl 1-(3-(3-amino-6-bromo-5-fluoro-picolinamido)pyridin-4-yl)piperidin-3-ylcarbamate

HRID 69977Notes

Reaction equation

HRID 69977 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH:11](F)[CH:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9]1.[NH2:23][C:24]1[C:25]([C:32](O)=[O:33])=[N:26][C:27]([Br:31])=[C:28]([F:30])[CH:29]=1>>[NH2:23][C:24]1[C:25]([C:32]([NH:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[N:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9]2)=[O:33])=[N:26][C:27]([Br:31])=[C:28]([F:30])[CH:29]=1

Participants

3

Reactant 2

HCID 726988793-Amino-6-bromo-5-fluoropicolinic acidHCID 76773287(+/-)-Tert-butyl 1-(3-aminopyridin-4-yl)-4-fluoropiperidin-3-ylcarbamate

Product 1

HCID 86669209(S)-tert-butyl 1-(3-(3-amino-6-bromo-5-fluoro-picolinamido)pyridin-4-yl)piperidin-3-ylcarbamateYield 40%

Procedure

Following Method 11 of Example 305, (+/−)-tert-butyl 1-(3-aminopyridin-4-yl)-4-fluoropiperidin-3-ylcarbamate and 3-amino-6-bromo-5-fluoro-picolinic acid were reacted yielding (S)-tert-butyl 1-(3-(3-amino-6-bromo-5-fluoro-picolinamido)pyridin-4-yl)piperidin-3-ylcarbamate (40%). LCMS (m/z): 509.0 (MH+), LC Rt=3.04 min.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-d3b32348e2d1487bb39558951df5849f
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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