3-Amino-6-bromopicolinic acid → tert-butyl (3S,5R)-1-(3-(3-amino-6-bromopicolinamido)pyridin-4-yl)-5-fluoropiperidin-3-ylcarbamate

HRID 69984Notes

Reaction equation

HRID 69984 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][C@H:12]([F:14])[CH2:11][C@H: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:31](O)=[O:32])=[N:26][C:27]([Br:30])=[CH:28][CH:29]=1>>[NH2:23][C:24]1[C:25]([C:31]([NH:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[N:8]2[CH2:13][C@H:12]([F:14])[CH2:11][C@H:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[CH2:9]2)=[O:32])=[N:26][C:27]([Br:30])=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 454804523-Amino-6-bromopicolinic acidHCID 68919601tert-butyl (3S,5R)-1-(3-aminopyridin-4-yl)-5-fluoropiperidin-3-ylcarbamate

Product 1

HCID 86669210tert-butyl (3S,5R)-1-(3-(3-amino-6-bromopicolinamido)pyridin-4-yl)-5-fluoropiperidin-3-ylcarbamate

Procedure

Following Method 11 of Example 305, tert-Butyl (3S,5R)-1-(3-aminopyridin-4-yl)-5-fluoropiperidin-3-ylcarbamate and 3-amino-6-bromopicolinic acid were coupled yielding after column chromatography tert-butyl (3S,5R)-1-(3-(3-amino-6-bromopicolinamido)pyridin-4-yl)-5-fluoropiperidin-3-ylcarbamate. LC/MS (m/z): 509.1/511.1 (MH+).

Sources & evidence

ORD record
ord-f52de13f530b4a0494cf483614d7b74c
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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