HCID 50913634, compound → HCID 58075690, compound

HRID 475874Notes

Reaction equation

HRID 475874 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:29]([CH3:31])[CH3:30])[C:17]4[CH2:22][CH2:21][CH:20]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[C:18]=4[N:19]=3)=[CH:9][C:8]=2[O:32][CH3:33])[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:29]([CH3:30])[CH3:31])[C:17]4[CH2:22][CH2:21][C@H:20]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[C:18]=4[N:19]=3)=[CH:9][C:8]=2[O:32][CH3:33])[CH:6]=1

Participants

4

Reactant 1

HCID 50913634HCID 50913634, compound

Product 1

HCID 58075690HCID 58075690, 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-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diamine (Example 4) was purified using chiral SFC to afford peak A (Example 4A) and peak B (Example 4B). 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 22 min, absorbance 268 nm, injection 5 μL of 2 mg/mL solution in methanol (multiple stacked injections), tR (peak A)=5.1 min, tR (peak B) 18.1 min. The absolute stereochemistry of individual enantiomers (Examples 4A and 4B) was not determined LC-MS and 1H NMR analytical data for the separated enantiomers was identical to the racemate (Example 4).

Workup

  1. customwas purified
  2. customto afford peak A (Example 4A) and peak B (Example 4B)
  3. custom=5.1 min, tR (peak B) 18.1 min

Sources & evidence

ORD record
ord-3501ee53e23f4fd09feaa0510e55655e
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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