GSK1360707F

GSK1360707F

Identifiers
IUPAC name (1R,6S)-1-(3,4-Dichlorophenyl)-6-(methoxymethyl)-4-azabicyclo[4.1.0]heptane
CAS Number	1013098-04-8 Y
PubChem CID	24802841
ChemSpider	32739425
UNII	9DE44WJ46X
Chemical and physical data
Formula	C14H17Cl2NO
Molar mass	286.20 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC[C@@]12C[C@@]1(CCNC2)c3ccc(c(c3)Cl)Cl
InChI InChI=1S/C14H17Cl2NO/c1-18-9-13-7-14(13,4-5-17-8-13)10-2-3-11(15)12(16)6-10/h2-3,6,17H,4-5,7-9H2,1H3/t13-,14-/m0/s1 Key:ICXJGCSEMJXNQF-KBPBESRZSA-N
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GSK1360707F is a potent and selective triple reuptake inhibitor.^[1] It is chemically related to amitifadine and NS-2359 (GSK-372,475). Until recently,^[when?] it was under development for the treatment of major depressive disorder; its development was put on hold for strategic reasons.^{[citation needed]}

Synthesis

1. BOC Protecting group.
2. Enolization and trapping with triflate group (cf Comins' reagent).
3. Suzuki reaction
4. Reduction (only 1 mol eq. LAH because N-BOC can be reduced to N-Me)
5. Trifluoroacetic acid (TFA) removal of protecting group.
6. Simmons–Smith reaction cyclopropanation.
7. Williamson ether synthesis (c.f. NS patents & paxil).

Transporter occupancy

GSK1360707F has recently (2013) been tested on baboons (Papio anubis) & humans for transporter occupancy using PET.^[3]

See also

• NS-2359

References