3-Amino-6-bromopicolinic acid → HCID 86669213, compound

HRID 69994Notes

Reaction equation

HRID 69994 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]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:11][C@H:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:9]1.[Br:30][C:31]1[N:36]=[C:35]([C:37](O)=[O:38])[C:34]([NH2:40])=[CH:33][CH:32]=1>>[NH2:40][C:34]1[C:35]([C:37]([NH:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[N:8]2[CH2:13][C@H:12]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:11][C@H:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:9]2)=[O:38])=[N:36][C:31]([Br:30])=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 454804523-Amino-6-bromopicolinic acidHCID 68919475tert-butyl (3S,5R)-1-(3-aminopyridin-4-yl)-5-(tert-butyldimethylsilyloxy)piperidin-3-ylcarbamate

Product 1

HCID 86669213HCID 86669213, compound

Procedure

Following Method 11 of Example 305, tert-butyl (3S,5R)-1-(3-aminopyridin-4-yl)-5-(tert-butyldimethylsilyloxy)piperidin-3-ylcarbamate and 6-bromo-3-aminopicolinic acid were coupled to yield tert-butyl (3S,5R)-1-(3-(3-amino-6-bromopicolinamido)pyridin-4-yl)-5-(tert-butyldimethylsilyloxy)piperidin-3-ylcarbamate. LCMS (m/z): 621.1/623.2 (MH+).

Sources & evidence

ORD record
ord-d07ef3f0eaea497fbd69b7ff8ab42622
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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