3,6-Dichloro-4-methylpyridazine → HCID 16748608, compound

HRID 914737Notes

Reaction equation

HRID 914737 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[CH3:8].[C@H:10]12[CH2:16][C@H:13]([NH:14][CH2:15]1)[CH2:12][N:11]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:14]2[CH2:15][C@@H:10]3[CH2:16][C@H:13]2[CH2:12][N:11]3[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:6][C:7]=1[CH3:8]

Participants

3

Reactant 2

HCID 879233,6-Dichloro-4-methylpyridazineHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 16748608HCID 16748608, compoundYield 56%

Procedure

3,6-Dichloro-4-methylpyridazine (Aldrich Chemical Company) 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 (56% yield). 1H NMR (CDCl3, 300 MHz) δ 1.41 (s, 4.5H), 1.43 (s, 4.5H), 1.90-2.09 (m, 2H), 2.31(s, 3H), 3.35-3.45 (m, 3H), 3.53-3.60(m, 1H), 4.56(s, 0.5H), 4.69(s, 0.5H), 4.90(s, 0.5H), 5.08(s, 0.5H), 6.48(s, 1H); MS (DCI/NH3) m/z 325 (M+H)+.

Sources & evidence

ORD record
ord-e912f2c641104e2387d183c83a33c1b2
Source dataset
uspto-grants-2007_09
Patent number
US07265115B2

Reaction notes

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