HCID 58075449, compound → HCID 58075332, compound

HRID 475902Notes

Reaction equation

HRID 475902 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]([NH:31][CH3:32])[C:17]4[CH2:22][CH2:21][CH:20]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=5)[C:18]=4[N:19]=3)=[CH:9][C:8]=2[O:33][CH3:34])[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]([NH:31][CH3:32])[C:17]4[CH2:22][CH2:21][C@H:20]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=5)[C:18]=4[N:19]=3)=[CH:9][C:8]=2[O:33][CH3:34])[CH:6]=1

Participants

4

Reactant 1

HCID 58075449HCID 58075449, compound

Product 1

HCID 58075332HCID 58075332, compound

Reagents, catalysts & solvents 2

HCID 280Carbon DioxideSolventHCID 887MethanolSolvent2×

Procedure

A racemic mixture of N2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-7-(3,4-difluorophenyl)-N4-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diamine (1.4 g, 2.345 mmol from Example 96) was purified using chiral SFC to afford 475 mg of peak A (Example 96A) and 435 mg of peak B (Example 96B). SFC Method: Chiralpak OJ-H (4.6×250 mm, 5 μM), 25% methanol (0.1% diethylamine) in CO2, 35° C., flow rate mL/min for 14 min, absorbance 268 nm, injection 5 μL of 2 mg/mL solution in methanol (multiple stacked injections), tR (peak A)=6.1 min, tR (peak B) 9.2 min. The absolute stereochemistry of individual enantiomers (Examples 96A and 96B) was not determined LC-MS and 1H NMR analytical data for the separated enantiomers was identical to the racemate (Example 96).

Workup

  1. customwas purified
  2. customto afford 475 mg of peak A (Example 96A) and 435 mg of peak B (Example 96B)
  3. custom=6.1 min, tR (peak B) 9.2 min

Sources & evidence

ORD record
ord-7ba787cb8de54ec59401fcf23d46db5b
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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