Trifluoroacetic acid → racemic trans 3-(6-benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentylamine

HRID 1257690Notes

Reaction equation

C(OC(=O)[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([N:13]2[C:24]3[C:16](=[CH:17][N:18]=[C:19]4[C:23]=3[CH:22]=[CH:21][N:20]4[S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:27])=[O:26])[N:15]=[N:14]2)[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>>[C:28]1([S:25]([N:20]2[CH:21]=[CH:22][C:23]3[C:19]2=[N:18][CH:17]=[C:16]2[C:24]=3[N:13]([C@H:10]3[CH2:11][CH2:12][C@H:8]([NH2:7])[CH2:9]3)[N:14]=[N:15]2)(=[O:26])=[O:27])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 131730637racemic trans [3-(6-benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentyl]-carbamic acid tert-butyl ester

Product 1

HCID 131730643racemic trans 3-(6-benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentylamineYield 76%

Procedure

A mixture of racemic trans [3-(6-benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentyl]-carbamic acid tert-butyl ester (1.00 g, 2.07 mmol) and trifluoroacetic acid (4 mL) was stirred at ambient temperature for 90 minutes. The mixture was purified by column chromatography (SCX-2, gradient: methanol to 2M NH3 in methanol) to afford 600 mg (76%) of racemic trans 3-(6-benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclopentylamine as an off white foam. LCMS (Method B, ESI): RT=2.40 min, m+H=383.

Workup

customThe mixture was purified by column chromatography (SCX-2, gradient: methanol to 2M NH3 in methanol)

Sources & evidence

ORD record: ord-4228ea4a770243c98e7cc0791ff0c537
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461328B2

Reaction notes

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