4'-Hydroxy-3',5'-dimethylacetophenone → 1-(5'-Fluoro-2'-methoxy-2,6-dimethyl-biphenyl-4-yl)-ethylamine

HRID 2422865Notes

Reaction equation

HRID 2422865 reaction equation
C(C1C=C(C(N)C)C=CC=1C1C=C(F)C=CC=1OC)C=C.CC1C(O)=C(C)C=C(C(C)=O)C=1.C(C1C=C(C(NS(C2C=CC(F)=C(F)C=2)(=O)=O)C)C=CC=1C1C=C(F)C=CC=1OC)C=C.[F:66][C:67]1[CH:68]=[CH:69][C:70]([O:84][CH3:85])=[C:71]([C:73]2[C:78]([CH3:79])=[CH:77][C:76]([CH:80]([NH2:82])[CH3:81])=[CH:75][C:74]=2[CH3:83])[CH:72]=1.[CH3:86][C:87]1[C:91]([S:92](Cl)(=[O:94])=[O:93])=[C:90]([CH3:96])[O:89][N:88]=1>>[F:66][C:67]1[CH:68]=[CH:69][C:70]([O:84][CH3:85])=[C:71]([C:73]2[C:78]([CH3:79])=[CH:77][C:76]([CH:80]([NH2:82])[CH3:81])=[CH:75][C:74]=2[CH3:83])[CH:72]=1.[F:66][C:67]1[CH:68]=[CH:69][C:70]([O:84][CH3:85])=[C:71]([C:73]2[C:78]([CH3:79])=[CH:77][C:76]([CH:80]([NH:82][S:92]([C:91]3[C:87]([CH3:86])=[N:88][O:89][C:90]=3[CH3:96])(=[O:94])=[O:93])[CH3:81])=[CH:75][C:74]=2[CH3:83])[CH:72]=1

Participants

7

Reactant 5

HCID 365814'-Hydroxy-3',5'-dimethylacetophenoneHCID 27363193,5-Dimethylisoxazole-4-sulfonyl chlorideHCID 67244664HCID 67244664, compoundHCID 67245690N-[1-(2-allyl-5'-fluoro-2'-methoxy-biphenyl-4-yl)-ethyl]-3,4-difluoro-benzenesulfonamideHCID 672463171-(5'-Fluoro-2'-methoxy-2,6-dimethyl-biphenyl-4-yl)-ethylamine

Product 2

HCID 672463171-(5'-Fluoro-2'-methoxy-2,6-dimethyl-biphenyl-4-yl)-ethylamineHCID 672468803,5-Dimethyl-isoxazole-4-sulfonic acid [1-(5'-fluoro-2'-methoxy-2,6-dimethyl-biphenyl-4-yl)-ethyl]-amide

Procedure

1-(5′-Fluoro-2′-methoxy-2,6-dimethyl-biphenyl-4-yl)-ethylamine was prepared in a similar manner to 1-(2-allyl-5′-fluoro-2′-methoxy-biphenyl-4-yl)-ethylamine (Example 34) using 3,5-dimethyl-4-hydroxy acetophenone instead of 3′-allyl-4′-hydroxyacetophenone. The title compound was prepared in a similar manner to N-[1-(2-allyl-5′-fluoro-2′-methoxy-biphenyl-4-yl)-ethyl]-3,4-difluoro-benzenesulfonamide (Example 34) using 1-(5′-fluoro-2′-methoxy-2,6-dimethyl-biphenyl-4-yl)-ethylamine and 3,5-dimethyl-isoxazole-4-sulfonyl chloride. MS (ESI) m/z: 433.3 [M+H]+.

Sources & evidence

ORD record
ord-bfa7e6d5465649dd812605c841f24fbf
Source dataset
uspto-grants-2011_06
Patent number
US07960365B2

Reaction notes

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