6-Aminopyridazine-3-carboxylic acid → 3-(6-Amino-pyridazine-3-carbonyl)-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

HRID 1850567Notes

Reaction equation

HRID 1850567 reaction equation
[NH2:1][C:2]1[N:7]=[N:6][C:5]([C:8]([OH:10])=O)=[CH:4][CH:3]=1.[C:11]([O:15][C:16]([N:18]1[CH:23]2[CH2:24][CH2:25][CH:19]1[CH2:20][NH:21][CH2:22]2)=[O:17])([CH3:14])([CH3:13])[CH3:12]>>[C:11]([O:15][C:16]([N:18]1[CH:19]2[CH2:25][CH2:24][CH:23]1[CH2:22][N:21]([C:8]([C:5]1[N:6]=[N:7][C:2]([NH2:1])=[CH:3][CH:4]=1)=[O:10])[CH2:20]2)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

3

Reactant 2

HCID 122004796-Aminopyridazine-3-carboxylic acidHCID 157409088-Boc-3,8-diaza-bicyclo(3.2.1)octane

Product 1

HCID 673553473-(6-Amino-pyridazine-3-carbonyl)-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl esterYield 51%

Procedure

Following general amide formation method 1, 6-amino-pyridazine-3-carboxylic acid (212 mg, 1.0 mmol) was combined with 3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (139 mg, 1.0 mmol), which gave 3-(6-Amino-pyridazine-3-carbonyl)-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester as a white solid (169 mg, 0.51 mmol) in 51% yield. MS m/z 334.4 (M+H)+.

Sources & evidence

ORD record
ord-0bfa1c5693e04cbb8ce47b81abe26ffd
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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