(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane → HCID 86590399, compound

HRID 914739Notes

Reaction equation

HRID 914739 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9].[C@H:13]12[CH2:19][C@H:16]([NH:17][CH2:18]1)[CH2:15][N:14]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:17]2[CH2:18][C@@H:13]3[CH2:19][C@H:16]2[CH2:15][N:14]3[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

3

Reactant 2

HCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptaneHCID 17861811Methyl 3,6-dichloropyridazine-4-carboxylate

Product 1

HCID 86590399HCID 86590399, compoundYield 41%

Procedure

Methyl 3,6-dichloropyridazine-4-carboxylate and tert-butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate, prepared as described in (J. Med. Chem., (1988) 31, 1598-1611), were processed as described in Example 2A to provide the title compound (41% yield). 1H NMR (CDCl3, 300 MHz) δ 1.42 (s, 4.5H), 1.47 (s, 4.5H), 1.90-2.11 (m, 2H), 2.86 (d, J=9.93 Hz, 1H), 3.40-3.62 (m, 2H), 3.72 (d, J=9.90 Hz, 1H), 3.93 (s, 3H), 3.51 (s, 0.5H), 4.63 (s, 0.5H), 5.05-5.15 (m, 1H), 7.49 (s, 1H); MS (DCI/NH3) m/z 368 (M+H)+.

Sources & evidence

ORD record
ord-fe78703507964e839b84e331240f0a45
Source dataset
uspto-grants-2007_09
Patent number
US07265115B2

Reaction notes

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