1-Bromo-2-methylpropane → 3-Isobutyl-2-(4-cyano-1-naphthylimino)-1-thia-3-azaspiro[4.4]nonane
Reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([N:13]=[C:14]2[NH:18][CH2:17][C:16]3([CH2:22][CH2:21][CH2:20][CH2:19]3)[S:15]2)=[CH:5][CH:4]=1)#[N:2].[CH2:23](Br)[CH:24]([CH3:26])[CH3:25]>>[CH2:23]([N:18]1[CH2:17][C:16]2([CH2:19][CH2:20][CH2:21][CH2:22]2)[S:15][C:14]1=[N:13][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[CH:24]([CH3:26])[CH3:25]Participants
3
Procedure
1-Amino-1-(hydroxymethyl)cyclopentane was synthesized as described in Method B1c. The 2-hydroxyethylamine was reacted with SOCl2 according to Method B7a to give 1-amino-1-(chloromethyl)cyclopentane HCl salt. 1-Amino-4-cyanonaphthalene was converted into 4-cyano-1-naphthyl isothiocyanate according to Method A2a, Step 3. The 2-chloroethylamine was reacted with 4-cyano-1-naphthyl isothiocyanate to Method C1a to give 2-(4-cyano-1-naphthylimino)-1-thia-3-azaspiro[4.4]nonane. The thiazolidine was reacted with isobutyl bromide according to Method D2b to give 3-isobutyl-2-(4-cyano-1-naphthylimino)-1-thia-3-azaspiro[4.4]nonane.
Sources & evidence
- ORD record
- ord-5d4544eba0224e4284350711bfb6644a
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353006B1
Reaction notes
Loading…