3-Amino-6-bromo-5-(trifluoromethyl)picolinohydrazide → 2-(5-(1,1,1-Trifluoro-2-(triisopropylsilyloxy)propan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyridin-3-amine

HRID 574213Notes

Reaction equation

HRID 574213 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[O:9][C:10]([C:13]([O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])([CH3:18])[C:14]([F:17])([F:16])[F:15])=[N:11][N:12]=2)[C:5]([NH2:30])=[CH:4][C:3]=1[C:31]([F:34])([F:33])[F:32].NC1C(C(NN)=O)=NC(Br)=C(C(F)(F)F)C=1.NC1C(C(NN)=O)=NC=C(C(F)(F)F)C=1>>[F:17][C:14]([F:15])([F:16])[C:13]([C:10]1[O:9][C:8]([C:6]2[C:5]([NH2:30])=[CH:4][C:3]([C:31]([F:32])([F:33])[F:34])=[CH:2][N:7]=2)=[N:12][N:11]=1)([O:19][Si:20]([CH:21]([CH3:22])[CH3:23])([CH:24]([CH3:26])[CH3:25])[CH:27]([CH3:28])[CH3:29])[CH3:18]

Participants

4

Reactant 3

HCID 867295953-Amino-6-bromo-5-(trifluoromethyl)picolinohydrazideHCID 867295986-Bromo-2-(5-(1,1,1-trifluoro-2-(triisopropylsilyloxy)propan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyridin-3-amineHCID 867296013-Amino-5-(trifluoromethyl)picolinohydrazide

Product 1

HCID 867296002-(5-(1,1,1-Trifluoro-2-(triisopropylsilyloxy)propan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyridin-3-amine

Procedure

The title compound was prepared analogously to 6-bromo-2-(5-(1,1,1-trifluoro-2-(triisopropylsilyloxy)propan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyridin-3-amine (Example 10, step 3) by replacing 3-amino-6-bromo-5-(trifluoromethyl)picolinohydrazide (Intermediate H) (step 1) with 3-amino-5-(trifluoromethyl)picolinohydrazide (Int. I); LCMS: Rt=1.66 min; [M+H]+ 499.3 Method 2minLC_v003.

Sources & evidence

ORD record
ord-593c3fb0886543dda573bd6972f2a9cc
Source dataset
uspto-grants-2015_05
Patent number
US09034879B2

Reaction notes

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