HCID 178437574, compound → HCID 178461702, compound

HRID 1523279Notes

Reaction equation

HRID 1523279 reaction equation
[F:1][C:2]([F:23])([F:22])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([CH:15]([C:17]3([NH2:21])[CH2:20][O:19][CH2:18]3)[CH3:16])[NH:13][CH:14]=2)=[CH:6][CH:5]=1>C(O)C>[F:23][C:2]([F:1])([F:22])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([C@@H:15]([C:17]3([NH2:21])[CH2:18][O:19][CH2:20]3)[CH3:16])[NH:13][CH:14]=2)=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 178437574HCID 178437574, compound

Product 1

HCID 178461702HCID 178461702, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Racemic 3-(1-{4-[4-(trifluoromethoxy)phenyl]-1H-imidazol-2-yl}ethyl)oxetan-3-amine (Example 9, 0.243 g, 0.743 mmol) was dissolved in ethanol (1 mL). Enantiomers were separated by chiral preparative HPLC under basic conditions at ambient temperature on a Chiralpak AD-H column (250*, 20 mm i.d) supplied by Daicel Chemical Industries. A flow rate of 18 mL/min was used with mobile phase A: heptane and B: IPA+0.1% diethylamine (v/v). Two Agilent 1200 prep pumps supplied a mobile phase with a composition of 20% B. Run time was 10 minutes per 0.1 mL injection volume. Detection was achieved using an Agilent 1200 multiple wavelength UV absorbance detector set at 220 nm.

Workup

  1. customEnantiomers were separated by chiral preparative HPLC under basic conditions at ambient temperature on a Chiralpak AD-H column (250*, 20 mm i.d)

Sources & evidence

ORD record
ord-90fa887c27e04f1cadcbf0e0d1e60d41
Source dataset
uspto-grants-2015_07
Patent number
US09079878B2

Reaction notes

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