8-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine → 3-(8-Diethoxymethyl-2-methyl-imidazo[1,2-a]pyridin-3-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

HRID 226045Notes

Reaction equation

HRID 226045 reaction equation
[CH2:1]([O:3][CH:4]([O:15][CH2:16][CH3:17])[C:5]1[C:6]2[N:7]([CH:11]=[C:12]([CH3:14])[N:13]=2)[CH:8]=[CH:9][CH:10]=1)[CH3:2].[CH2:18]([CH:20]([C:23]1[C:24]2[N:25]([C:30](I)=[C:31]([CH3:33])[N:32]=2)[N:26]=[C:27]([CH3:29])[CH:28]=1)[CH2:21][CH3:22])[CH3:19]>>[CH2:1]([O:3][CH:4]([O:15][CH2:16][CH3:17])[C:5]1[C:6]2[N:7]([C:11]([C:30]3[N:25]4[N:26]=[C:27]([CH3:29])[CH:28]=[C:23]([CH:20]([CH2:18][CH3:19])[CH2:21][CH3:22])[C:24]4=[N:32][C:31]=3[CH3:33])=[C:12]([CH3:14])[N:13]=2)[CH:8]=[CH:9][CH:10]=1)[CH3:2]

Participants

3

Reactant 2

HCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazineHCID 688574518-Diethoxymethyl-2-methyl-imidazo[1,2-a]pyridine

Product 1

HCID 688555073-(8-Diethoxymethyl-2-methyl-imidazo[1,2-a]pyridin-3-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazineYield 72%

Procedure

Using a procedure analogous to Example 16B, 8-diethoxymethyl-2-methyl-imidazo[1,2-a]pyridine (1.70 g, 7.26 mmol) and 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (2.49 g, 7.26 mmol) give the title compound (2.34 g, 5.21 mmol, 72%). 1H NMR (CDCl3): δ. 0.92 (t, J=7.5 Hz, 3H), 0.93 (t, J=7.5 Hz, 3H), 1.31 (t, J=7.1 Hz, 3H), 1.33 (t, J=7.1 Hz, 3H), 1.79-1.93 (m, 4H), 2.14 (s, 3H), 2.44 (s, 6H), 3.34-3.42 (m, 1H), 3.67-3.94 (m, 4H), 6.26 (s, 1H), 6.73 (s, 1H), 6.73-6.80 (m, 1H), 7.44-7.54 (m, 2H) ppm. ES-MS (m/z): calcd for C26H35N5O2 (M+H)+: 450.6. found: 450.3.

Sources & evidence

ORD record
ord-97f51d7c76c84b95a302ff3a0e888697
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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