Ether hydrochloride → 3-(6-Amino-3-pyridinyl)-3,8-diazabicyclo[3.2.1]octane trihydrochloride

HRID 914743Notes

Reaction equation

HRID 914743 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:14][CH:13]3[N:15](C(OC(C)(C)C)=O)[CH:10]([CH2:11][CH2:12]3)[CH2:9]2)=[CH:4][CH:3]=1.[ClH:23].CCOCC>>[ClH:23].[ClH:23].[ClH:23].[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:14][CH:13]3[NH:15][CH:10]([CH2:11][CH2:12]3)[CH2:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 10953452Ether hydrochlorideHCID 67357179Tert-butyl 3-(6-amino-3-pyridinyl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate

Product 1

HCID 692885873-(6-Amino-3-pyridinyl)-3,8-diazabicyclo[3.2.1]octane trihydrochlorideYield 72%

Procedure

The product from Example 11A was treated with 1M HCl/ether to provide the title compound (72% yield). 1H NMR (DMSO-d6, 300 MHz) δ 2.00 (s, 4H), 3.2 (d, J=11 Hz, 2H), 3.4 (s, J=11 Hz, 2H), 4.20 (br s, 2H), 5.80 (s, 2H, exchangeable), 7.00, (d, J=8.5 Hz, 1H), 7.40 (br s, 1H), 7.80 (br s, 2H, exchangeable), 7.9-8.0 (m, 1H), 9.10 (br s, 2H, exchangeable).

Sources & evidence

ORD record
ord-492491d69a544df0bcbf67a1903ec91e
Source dataset
uspto-grants-2007_09
Patent number
US07265115B2

Reaction notes

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