HCID 178423753, compound → (cis)-4-[7-methyl-4,5,6,7-tetrahydro-2H-indazol-4-yl]benzonitrile

HRID 1624052Notes

Reaction equation

HRID 1624052 reaction equation
[CH3:1][CH:2]1[C:10]2[C:6](=[CH:7][NH:8][N:9]=2)[CH:5]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[CH2:4][CH2:3]1.C[C@@H]1C2C(=CNN=2)[C@@H](C2C=CC(C#N)=CC=2)CC1>CCO>[CH3:1][C@H:2]1[C:10]2[C:6](=[CH:7][NH:8][N:9]=2)[C@@H:5]([C:11]2[CH:12]=[CH:13][C:14]([C:15]#[N:16])=[CH:17][CH:18]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 178423753HCID 178423753, compoundHCID 178461186HCID 178461186, compound

Product 1

HCID 178461185(cis)-4-[7-methyl-4,5,6,7-tetrahydro-2H-indazol-4-yl]benzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(+/−)-(cis/trans)-4-[7-Methyl-4,5,6,7-tetrahydro-2H-indazol-4-yl]benzonitrile (0.36 g, 1.52 mmol) and (+/−)-(trans)-4-[7-methyl-4,5,6,7-tetrahydro-2H-indazol-4-yl]benzonitrile (0.18 g, 0.76 mmol) are combined and the single enantiomers are obtained by chiral chromatography (Chiralpak AD-H, 4.6×150 mm, 100% EtOH 0.2% DMEA, 225 mm) to give (cis)-4-[7-methyl-4,5,6,7-tetrahydro-2H-indazol-4-yl]benzonitrile-isomer 2, (0.05 g, 27%) as the second eluting isomer. ES/MS m/z 238 (M+H), Tr=2.988 min. (trans)-4-[7-Methyl-4,5,6,7-tetrahydro-2H-indazol-4-yl]benzonitrile-isomer 4, Example 61 (0.07 g, 19%). ES/MS m/z 238 (M+H).

Sources & evidence

ORD record
ord-8f9eb791cc60452ea1437e58a1853fba
Source dataset
uspto-grants-2014_07
Patent number
US08778984B2

Reaction notes

Loading…