Hydroxylamine → 2-(Difluoromethoxy)-4-fluorobenzonitrile

HRID 1172696Notes

Reaction equation

HRID 1172696 reaction equation
[F:1][CH:2]([F:36])[O:3][C:4]1[CH:9]=[C:8](OC(C2SC(C3C=CC(C(F)(F)F)=CC=3)=NC=2C)CC)[CH:7]=[CH:6][C:5]=1[C:30]1NC(=O)O[N:31]=1.NO.[F:39]C(F)OC1C=C([O:48][C@@H:49]([C:52]2[S:56][C:55]([C:57]3[CH:62]=[CH:61][C:60]([C:63]([F:66])([F:65])[F:64])=[CH:59][CH:58]=3)=[N:54][C:53]=2[CH2:67][N:68]2[CH2:73][CH2:72][CH:71]([C:74]([F:77])([F:76])[F:75])[CH2:70][CH2:69]2)[CH2:50][CH3:51])C=CC=1C1NC(=O)ON=1>>[F:66][C:63]([F:64])([F:65])[C:60]1[CH:61]=[CH:62][C:57]([C:55]2[S:56][C:52]([C@H:49]([OH:48])[CH2:50][CH3:51])=[C:53]([CH2:67][N:68]3[CH2:73][CH2:72][CH:71]([C:74]([F:76])([F:75])[F:77])[CH2:70][CH2:69]3)[N:54]=2)=[CH:58][CH:59]=1.[F:1][CH:2]([F:36])[O:3][C:4]1[CH:9]=[C:8]([F:39])[CH:7]=[CH:6][C:5]=1[C:30]#[N:31]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 136014642(+)-3-(2-Difluoromethoxy-4-{(r)-1-[2-(4-trifluoromethyl-phenyl)-4-(4-trifluoromethyl-piperidin-1-ylmethyl)-thiazol-5-yl]-propoxy}-phenyl)-4h-1,2,4-oxadiazol-5-oneHCID 1360146463-(2-difluoromethoxy-4-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propoxy}-phenyl)-4H-1,2,4-oxadiazol-5-one

Product 2

HCID 592953882-(Difluoromethoxy)-4-fluorobenzonitrileHCID 59556315(R)-1-[2-(4-trifluoromethyl-phenyl)-4-(4-trifluoromethyl-piperidin-1-ylmethyl)-thiazol-5-yl]-propan-1-ol

Procedure

According to the method described for 3-(2-difluoromethoxy-4-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propoxy}-phenyl)-4H-1,2,4-oxadiazol-5-one (except for the hydroxylamine addition step which was performed under microwave irradiation at 100° C. for 2 h), (+)-3-(2-difluoromethoxy-4-{(R)-1-[2-(4-trifluoromethyl-phenyl)-4-(4-trifluoromethyl-piperidin-1-ylmethyl)-thiazol-5-yl]-propoxy}-phenyl)-4H-1,2,4-oxadiazol-5-one was obtained from (R)-1-[2-(4-trifluoromethyl-phenyl)-4-(4-trifluoromethyl-piperidin-1-ylmethyl)-thiazol-5-yl]-propan-1-ol and 2-difluoromethoxy-4-fluoro-benzonitrile.

Sources & evidence

ORD record
ord-aae790e168854a3aae60f6ad40edf5d7
Source dataset
uspto-grants-2010_11
Patent number
US07834030B2

Reaction notes

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