HCID 58075824, compound → HCID 58075659, compound

HRID 475907Notes

Reaction equation

HRID 475907 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[C:16]([N:34]([CH3:36])[CH3:35])[C:17]4[CH2:22][CH2:21][CH:20]([C:23]5[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=5)[C:18]=4[N:19]=3)=[CH:9][C:8]=2[O:37][CH3:38])[CH:6]=1>C(=O)=O.CO>[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[C:16]([N:34]([CH3:35])[CH3:36])[C:17]4[CH2:22][CH2:21][C@H:20]([C:23]5[CH:24]=[CH:25][C:26]([O:29][C:30]([F:32])([F:33])[F:31])=[CH:27][CH:28]=5)[C:18]=4[N:19]=3)=[CH:9][C:8]=2[O:37][CH3:38])[CH:6]=1

Participants

4

Reactant 1

HCID 58075824HCID 58075824, compound

Product 1

HCID 58075659HCID 58075659, compound

Reagents, catalysts & solvents 2

HCID 280Carbon DioxideSolventHCID 887MethanolSolvent2×

Procedure

A racemic mixture of N2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-N4,N4-dimethyl-7-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diamine (235 mg, 0.431 mmol from Example 100) was purified using chiral SFC to afford 29.2 mg of peak A (Example 100A) and 29.2 mg of peak B (Example 100B). 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 11 min, absorbance 268 nm, injection 5 μL of 2 mg/mL solution in methanol (multiple stacked injections), tR (peak A)=3.7 min, tR (peak B) 8.4 min. The absolute stereochemistry of individual enantiomers (Examples 100A and 100B) was not determined. LC-MS and 1H NMR analytical data for the separated enantiomers was identical to the racemate (Example 100).

Workup

  1. customwas purified
  2. customto afford 29.2 mg of peak A (Example 100A) and 29.2 mg of peak B (Example 100B)
  3. custom=3.7 min, tR (peak B) 8.4 min

Sources & evidence

ORD record
ord-397cec61d1ac4c1f80cd4674b0334de5
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

Loading…