(1R,5S)-3-methyl-8-(6-nitropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane → 5-(3-Methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)pyridin-2-amine

HRID 449704Notes

Reaction equation

HRID 449704 reaction equation
ClC1C=C(NC2C=CC(N3CCC(O)(C)CC3)=CN=2)C(=O)N(C)N=1.[CH3:25][N:26]1[CH2:32][C@H:31]2[N:33]([C:34]3[CH:35]=[N:36][C:37]([N+:40]([O-])=O)=[CH:38][CH:39]=3)[C@H:28]([CH2:29][CH2:30]2)[CH2:27]1>CO.[Pd]>[CH3:25][N:26]1[CH2:32][CH:31]2[N:33]([C:34]3[CH:39]=[CH:38][C:37]([NH2:40])=[N:36][CH:35]=3)[CH:28]([CH2:29][CH2:30]2)[CH2:27]1

Participants

5

Reactant 2

HCID 66742801(1R,5S)-3-methyl-8-(6-nitropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octaneHCID 667429326-chloro-4-(5-(4-hydroxy-4-methylpiperidin-1-yl)pyridin-2-ylamino)-2-methylpyridazin-3(2H)-one

Product 1

HCID 667431655-(3-Methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

This reaction was carried out under similar conditions to those described above in preparation of 6-chloro-4-(5-(4-hydroxy-4-methylpiperidin-1-yl)pyridin-2-ylamino)-2-methyl-pyridazin-3(2H)-one. (1R,5S)-3-methyl-8-(6-nitropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane (500 mg, 2.01 mmol) in methanol (15 ml) was hydrogenated at 50 psi with 10% Pd/C (42.9 mg, 40.3 umol) overnight. The catalyst was filtered off and the resultant filtrate was concentrated in vacuo to afford 5-(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)pyridin-2-amine. The product was carried to next reaction without further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe resultant filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b804edee57124fbe80d9aeee502657be
Source dataset
uspto-grants-2013_07
Patent number
US08481540B2

Reaction notes

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