3-Amino-6-bromopicolinic acid → 3-amino-6-bromo-N-(4-(3-(tert-butyldimethylsilyloxy)piperidin-1-yl)pyridin-3-yl)picolinamide

HRID 69920

Reaction equation

HRID 69920 reaction equation
C([C:5]1[C:10]([NH2:11])=[C:9]([N:12]2[CH2:17][CH2:16][CH2:15][CH:14]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:13]2)[CH:8]=[CH:7][N:6]=1)(C)(C)C.[NH2:26][C:27]1[C:28]([C:34](O)=[O:35])=[N:29][C:30]([Br:33])=[CH:31][CH:32]=1>>[NH2:26][C:27]1[C:28]([C:34]([NH:11][C:10]2[CH:5]=[N:6][CH:7]=[CH:8][C:9]=2[N:12]2[CH2:17][CH2:16][CH2:15][CH:14]([O:18][Si:19]([C:22]([CH3:23])([CH3:24])[CH3:25])([CH3:21])[CH3:20])[CH2:13]2)=[O:35])=[N:29][C:30]([Br:33])=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 454804523-Amino-6-bromopicolinic acidHCID 86669190Tert-butyl (+/-)-4-(3-(tert-butyldimethylsilyloxy)piperidin-1-yl)pyridin-3-amine

Product 1

HCID 866691923-amino-6-bromo-N-(4-(3-(tert-butyldimethylsilyloxy)piperidin-1-yl)pyridin-3-yl)picolinamide

Procedure

Following Method 11 of Example 305, tert-butyl (+/−)-4-(3-(tert-butyldimethylsilyloxy)piperidin-1-yl)pyridin-3-amine was coupled to 3-amino-6-bromopicolinic acid yielding 3-amino-6-bromo-N-(4-(3-(tert-butyldimethylsilyloxy)-piperidin-1-yl)pyridin-3-yl)picolinamide. LCMS (m/z): 506.2 (MH+); LC Rt=4.03 min.

Sources & evidence

ORD record
ord-101accd70817478cbf41745f620923f4
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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