3-Amino-6-bromopicolinic acid → trans-(+/-)-Tert-butyl 1-(3-(3-amino-6-bromopicolinamido)pyridin-4-yl)-3-(tert-butyldimethylsilyloxy)piperidin-4-yl-carbamate

HRID 69931Notes

Reaction equation

HRID 69931 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][C@@H:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:10]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:9]1.[NH2:30][C:31]1[C:32]([C:38](O)=[O:39])=[N:33][C:34]([Br:37])=[CH:35][CH:36]=1>>[NH2:30][C:31]1[C:32]([C:38]([NH:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[N:8]2[CH2:13][CH2:12][C@@H:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18])[C@H:10]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:9]2)=[O:39])=[N:33][C:34]([Br:37])=[CH:35][CH:36]=1

Participants

3

Reactant 2

HCID 454804523-Amino-6-bromopicolinic acidHCID 68184619trans-(+/-)-Tert-butyl 1-(3-aminopyridin-4-yl)-3-(tert-butyldimethylsilyloxy)piperidin-4-ylcarbamate

Product 1

HCID 88862445trans-(+/-)-Tert-butyl 1-(3-(3-amino-6-bromopicolinamido)pyridin-4-yl)-3-(tert-butyldimethylsilyloxy)piperidin-4-yl-carbamateYield 20%

Procedure

Following Method 11 of Example 305, trans-(+/−)-tert-butyl 1-(3-aminopyridin-4-yl)-3-(tert-butyldimethylsilyloxy)piperidin-4-ylcarbamate and 3-amino-6-bromo-picolinic acid was reacted yielding trans-(+/−)-tert-butyl 1-(3-(3-amino-6-bromopicolinamido)pyridin-4-yl)-3-(tert-butyldimethylsilyloxy)piperidin-4-yl-carbamate, (20%). LCMS (m/z): 623.2 (MH+); LC Rt=4.12 min.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-2a8990aa76cf4543876a3580a9d6ca16
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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