Methanol → HCID 58075451, compound

HRID 451150Notes

Reaction equation

HRID 451150 reaction equation
[N:1]1([C:5]2[C:6]3[CH2:28][CH2:27][CH:26]([C:29]4[CH:34]=[CH:33][CH:32]=[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.CO.CO.C(Cl)(Cl)Cl>C(=O)=O>[N:1]1([C:5]2[C:6]3[CH2:28][CH2:27][C@H:26]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=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

Participants

5

Reactant 3

HCID 887MethanolHCID 21584188Chloroform methanolHCID 50913636HCID 50913636, compound

Product 1

HCID 58075451HCID 58075451, compound

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

A racemic mixture of 4-(azetidin-1-yl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine (Example 6) was purified using chiral SFC to afford peak A (Example 6A) and peak B (Example 6B). SFC Method: Chiralpak OJ-H (4.6×250 mm, 5 μM), 35% methanol (0.1% diethylamine) in CO2, 35° C., flow rate 2.0 mL/min for 30 min, absorbance 268 nm, injection 5 μL of 2 mg/mL solution in 50:50 methanol/chloroform (multiple stacked injections), tR (peak A)=5.9 min, tR (peak B) 24.6 min. The absolute stereochemistry of individual enantiomers (Examples 6A and 6B) was not determined LC-MS and 1H NMR analytical data for the separated enantiomers was identical to the racemate (Example 6).

Workup

  1. customwas purified
  2. customto afford peak A (Example 6A) and peak B (Example 6B)
  3. custom=5.9 min, tR (peak B) 24.6 min

Sources & evidence

ORD record
ord-5d424159f4b44aed8a32ddba6efa1bdb
Source dataset
uspto-grants-2013_07
Patent number
US08486952B2

Reaction notes

Loading…