Bromocyclopentane → 2-(4-Methoxycarbonyl-2-methylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane

HRID 276622Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]2[S:16][CH2:15][C:14]3([CH2:20][CH2:19][CH2:18][CH2:17]3)[NH:13]2)=[C:7]([CH3:21])[CH:6]=1)=[O:4].[CH:22]1(Br)[CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]2[S:16][CH2:15][C:14]3([CH2:20][CH2:19][CH2:18][CH2:17]3)[N:13]2[CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:7]([CH3:21])[CH:6]=1)=[O:4]

Participants

Reactant 2

HCID 8728Bromocyclopentane

HCID 178498120HCID 178498120, compound

Product 1

HCID 183160122-(4-Methoxycarbonyl-2-methylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane

Procedure

Methyl 4-amino-3-methylbenzoate was converted to 4-methoxycarbonyl-2-methylphenyl isothiocyanate according to Method A2b. 1-Hydroxymethylcyclopentanamine was prepared according to Method B1c. The 2-hydroxyethylamine was sequentially reacted with SOCl2 and 4-methoxycarbonyl-2-methylphenyl isothiocyanate according to Method C2a to give 2-(4-methoxycarbonyl-2-methylphenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with cyclopentyl bromide according to Method D2h to give 2-(4-methoxycarbonyl-2-methylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane.

Sources & evidence

ORD record: ord-485bbec401464f57b2c3793d24f8f013
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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