5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate → HCID 16046965, compound

HRID 1690692Notes

Reaction equation

HRID 1690692 reaction equation
O=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])[CH:5]=[CH:4][C:3]1=2.Cl.[CH2:21]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([NH:37]N)[CH:32]=2)=[CH:27][CH:26]=1)[CH2:22][CH2:23][CH3:24]>>[CH2:21]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:32]=[C:33]3[C:34]([C:11]4[CH2:10][CH2:9][C:8]5[CH:7]=[C:6]([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])[CH:5]=[CH:4][C:3]=5[C:2]=4[NH:37]3)=[CH:35][CH:36]=2)=[CH:27][CH:26]=1)[CH2:22][CH2:23][CH3:24]

Participants

3

Reactant 2

HCID 110983845-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonateHCID 66904838(4'-Butyl-biphenyl-3-yl)-hydrazine hydrochloride

Product 1

HCID 16046965HCID 16046965, compound

Procedure

The title material is prepared by reacting Trifluoro-methanesulfonic acid 5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl ester and (4′-Butyl-biphenyl-3-yl)-hydrazine hydrochloride (example 70, step 2) in an analogous manner and similar yield to example 1, step 3 except that purification is accomplished by reverse phase UV triggered HPLC. 1H NMR (400 MHz, d6-DMSO) d 11.63 (s, 1H), 7.78 (m, 2H), 7.58 (m, 4H), 7.46 (s, 1H), 7.33 (d, J=6.7 Hz, 1H), 7.28 (m, 2H), 3.09 (m, 2H), 2.95 (m, 2H), 2.64 (m, 2H), 1.60 (m, 2H), 1.35 (m, 2H), 0.94 (m, 3H); LC/MS calculated for [M+H]+ C27H25F3NO3S: 500.5, found: 500.0.

Workup

  1. customsimilar yield to example 1, step 3 except that purification

Sources & evidence

ORD record
ord-48cc65cd0d3e4e35a0e2005cf2b59b32
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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