6-Aminonicotinic acid → 5-(6-Amino-pyridine-3-carbonyl)-(R,R)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

HRID 627372Notes

Reaction equation

HRID 627372 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]2[CH2:14][C@@H:9]1[CH2:10][NH:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][N:17]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]2[CH2:14][C@@H:9]1[CH2:10][N:11]2[C:20]([C:19]1[CH:18]=[N:17][C:16]([NH2:15])=[CH:24][CH:23]=1)=[O:21])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 184966-Aminonicotinic acidHCID 11860399N-Boc-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 673554665-(6-Amino-pyridine-3-carbonyl)-(R,R)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl esterYield 31%

Procedure

Using amide formation method 1, (R,R)-2,5-Diaza-bicyclo[2.2.1]heptane-2-c arboxylic acid tert-butyl ester (1.0 g, 4.26 mmol, 1.0 eq) was combined with 6-Amino-nicotinic acid (588 mg, 4.26 mmol, 1.0 eq) to give 5-(6-Amino-pyridine-3-carbonyl)-(R,R)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (420 mg, 31% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.35-1.40 (m, 3H) 1.40-1.51 (m, 9H) 1.89 (br. s., 2H) 3.31-3.50 (m, 2H) 3.55 (d, J=9.09 Hz, 1H) 3.67 (dd, J=13.14, 6.57 Hz, 1H) 4.50 (br. s., 1H) 4.64 (br. s., 1H) 4.91 (br. s., 1H) 6.51 (d, J=6.57 Hz, 1H) 7.64 (br. s., 1H) 8.24 (br. s., 1H); MS m/z 637.0 (M+H)+.

Sources & evidence

ORD record
ord-1e52b8ff44f3420083296c7face2b170
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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