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

HRID 1850601Notes

Reaction equation

HRID 1850601 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].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.CCOC(C)=O>[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

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)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%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-amino-pyridazine-3-carboxylic acid (212 mg, 1.0 mmol) in DMF (5 mL) was added 3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (139 mg, 1.0 mmol), HATU (456 mg, 1.2 mmol) and N,N-diisopropylethylamine (0.52 mL, 3.0 mmol). The mixture was stirred at room temperature overnight after which it was diluted with EtOAc, washed with brine, dried over Na2SO4, concentrated and purified over normal silica with 0-20% MeOH/DCM which gave a white solid (169 mg, 0.51 mmol). MS m/z 334.4 (M+H)+.

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. custompurified over normal silica with 0-20% MeOH/DCM which

Sources & evidence

ORD record
ord-8a3d18828b3c4c2ba675a0cc2a07dd56
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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