HCID 58075434, compound → HCID 58075290, compound

HRID 451180Notes

Reaction equation

HRID 451180 reaction equation
[N:1]1([C:5]2[C:6]3[CH2:28][CH2:27][CH:26]([C:29]4[CH:34]=[CH:33][C:32]([O:35][C:36]([F:39])([F:38])[F:37])=[CH:31][CH:30]=4)[C:7]=3[N:8]=[C:9]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH:22]=[C:21]([Cl:23])[N:20]=[CH:19]4)=[C:14]([O:24][CH3:25])[CH:13]=3)[N:10]=2)[CH2:4][CH2:3][CH2:2]1>C(=O)=O.CO>[N:1]1([C:5]2[C:6]3[CH2:28][CH2:27][C@H:26]([C:29]4[CH:34]=[CH:33][C:32]([O:35][C:36]([F:37])([F:38])[F:39])=[CH:31][CH:30]=4)[C:7]=3[N:8]=[C:9]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH:22]=[C:21]([Cl:23])[N:20]=[CH:19]4)=[C:14]([O:24][CH3:25])[CH:13]=3)[N:10]=2)[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 1

HCID 58075434HCID 58075434, compound

Product 1

HCID 58075290HCID 58075290, compound

Reagents, catalysts & solvents 2

HCID 280Carbon DioxideSolventHCID 887MethanolSolvent2×

Procedure

A racemic mixture of 4-(azetidin-1-yl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-7-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine (92 mg, 0.165 mmol from Example 101) was purified using chiral SFC to afford 37.6 mg of peak A (Example 101A) and 39.1 mg of peak B (Example 101B). SFC Method: Chiralpak OJ-H (4.6×250 mm, 5 μM), 30% methanol (0.1% diethylamine) in CO2, 35° C., flow rate 2.0 mL/min for 18 min, absorbance 268 nm, injection 5 μL of 2 mg/mL solution in methanol (multiple stacked injections), tR (peak A)=4.7 min, tR (peak B) 13.6 min. The absolute stereochemistry of individual enantiomers (Examples 101A and 101B) was not determined LC-MS and 1H NMR analytical data for the separated enantiomers was identical to the racemate (Example 101).

Workup

  1. customwas purified
  2. customto afford 37.6 mg of peak A (Example 101A) and 39.1 mg of peak B (Example 101B)
  3. custom=4.7 min, tR (peak B) 13.6 min

Sources & evidence

ORD record
ord-596eabc9510741aca03b995c7d349649
Source dataset
uspto-grants-2013_07
Patent number
US08486952B2

Reaction notes

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