6-Bromo-5-fluoropicolinic Acid → (S)-tert-butyl 1-(3-(6-bromo-5-fluoropicolinamido)pyridin-4-yl)piperidin-3-ylcarbamate

HRID 69941Notes

Reaction equation

HRID 69941 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][CH2:11][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:9]1.[Br:22][C:23]1[N:28]=[C:27]([C:29](O)=[O:30])[CH:26]=[CH:25][C:24]=1[F:32]>>[Br:22][C:23]1[N:28]=[C:27]([C:29]([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:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[CH2:9]2)=[O:30])[CH:26]=[CH:25][C:24]=1[F:32]

Participants

3

Reactant 2

HCID 534011946-Bromo-5-fluoropicolinic AcidHCID 59332360(S)-tert-Butyl (1-(3-aminopyridin-4-yl)piperidin-3-yl)carbamate

Product 1

HCID 86669196(S)-tert-butyl 1-(3-(6-bromo-5-fluoropicolinamido)pyridin-4-yl)piperidin-3-ylcarbamate

Procedure

Following Method 11 (Example 305), (S)-tert-butyl 1-(3-aminopyridin-4-yl)piperidin-3-ylcarbamate was coupled to 6-bromo-5-fluoropicolinic acid yielding crude (S)-tert-butyl 1-(3-(6-bromo-5-fluoropicolinamido)pyridin-4-yl)piperidin-3-ylcarbamate (92%) which was used as is. LCMS (m/z): 496.2 (MH+); LC Rt=2.90 min.

Sources & evidence

ORD record
ord-cc96aeec01f8469aa6df713ed46decb2
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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