6-Amino-4-methylnicotinic acid → HCID 67357152, compound

HRID 627377Notes

Reaction equation

HRID 627377 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][NH:11][CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:16][C:17]1[CH:25]=[C:24]([CH3:26])[C:20]([C:21](O)=[O:22])=[CH:19][N:18]=1>>[C:1]([O:5][C:6]([N:8]1[CH:9]2[CH2:15][CH2:14][CH:13]1[CH2:12][N:11]([C:21]([C:20]1[CH:19]=[N:18][C:17]([NH2:16])=[CH:25][C:24]=1[CH3:26])=[O:22])[CH2:10]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 99641496-Amino-4-methylnicotinic acidHCID 157409088-Boc-3,8-diaza-bicyclo(3.2.1)octane

Product 1

HCID 67357152HCID 67357152, compoundYield 55.3%

Procedure

Following general amide formation method 1, 3,8-Diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (279 mg, 1.31 mmol, 1.0 eq) was combined with 6-Amino-4-methylnicotinic acid (200 mg, 1.31 mmol, 1.0 eq) to give 3-(6-Amino-4-methyl-pyridine-3-carbonyl)-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (251 mg) in 55% yield. MS m/z 347.0 (M+H)+.

Sources & evidence

ORD record
ord-870792cf2f764d71a91b0bd7672b5c67
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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