1-Bromo-2-methylpropane → 2-(5-Cyanothienylimino)-1-isobutyl-3-thia-1-azaspiro[4.4]nonane
Reaction equation
[C:1]([C:3]1[S:7][C:6]([N:8]=[C:9]2[S:13][CH2:12][C:11]3([CH2:17][CH2:16][CH2:15][CH2:14]3)[NH:10]2)=[CH:5][CH:4]=1)#[N:2].[CH2:18](Br)[CH:19]([CH3:21])[CH3:20]>>[C:1]([C:3]1[S:7][C:6]([N:8]=[C:9]2[S:13][CH2:12][C:11]3([CH2:14][CH2:15][CH2:16][CH2:17]3)[N:10]2[CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:5][CH:4]=1)#[N:2]Participants
3
Procedure
2-Cyano-5-nitrothiophene was reduced to 2-amino-5-cyanothiophene according to Method A1a. The aminothiophene was converted to 5-cyano-1-thiophene isothiocyanate according to Method A2b. 1-Hydroxymethylcyclopentanamine was prepared according to Method B1c. The 2-hydroxyethylamine was converted to 1-chloromethylcyclopentanamine HCl salt according to Method B7e. 1-Chloromethylcyclopentanamine HCl salt was reacted with 5-cyano-1-thiophene isothiocyanate according to Method C1e to give 2-(5-cyanothienylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with isobutyl bromide according to Method D2a to give 2-(5-cyanothienylimino)-1-isobutyl-3-thia-1-azaspiro[4.4]nonane.
Sources & evidence
- ORD record
- ord-07672c50948541cb94c5963cce64e0e8
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
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