7,7-Dimethyl-7,8-dihydro-3H-cyclopenta[4,5]thieno[2,3-d]pyridazin-4(6H)-one → 4-Chloro-2-{4,4-dimethyl-9-oxo-7-thia-10,11-diazatricyclo[6.4.0.02,6]dodeca-1(8),2(6),11-trien-10-yl}pyridine-3-carbaldehyde

HRID 1411990Notes

Reaction equation

HRID 1411990 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:13][C:12]2[S:11][C:10]3[C:9](=[O:14])[NH:8][N:7]=[CH:6][C:5]=3[C:4]=2[CH2:3]1.Br[C:17]1[N:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:18]=1[CH:19]=[O:20]>>[Cl:25][C:21]1[CH:22]=[CH:23][N:24]=[C:17]([N:8]2[N:7]=[CH:6][C:5]3[C:4]4[CH2:3][C:2]([CH3:15])([CH3:1])[CH2:13][C:12]=4[S:11][C:10]=3[C:9]2=[O:14])[C:18]=1[CH:19]=[O:20]

Participants

3

Reactant 2

HCID 866837837,7-Dimethyl-7,8-dihydro-3H-cyclopenta[4,5]thieno[2,3-d]pyridazin-4(6H)-oneHCID 866839142-Bromo-4-chloropyridine-3-carbaldehyde

Product 1

HCID 866845164-Chloro-2-{4,4-dimethyl-9-oxo-7-thia-10,11-diazatricyclo[6.4.0.02,6]dodeca-1(8),2(6),11-trien-10-yl}pyridine-3-carbaldehyde

Procedure

Following the procedures as described in Example 108a, and starting with 282h (330 mg, 1.5 mmol) and 2-bromo-4-chloronicotinaldehyde (950 mg, 4.5 mmol), 282i was obtained as a yellow solid (260 mg, 48%). MS-ESI: [M+H]+ 359.9

Sources & evidence

ORD record
ord-9c606e081e4b41bf826251602770233a
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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