HCID 58075483, compound → HCID 58075454, compound

HRID 475906Notes

Reaction equation

HRID 475906 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]4[CH2:37][C:36]([F:39])([F:38])[CH2:35]4)[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:40][CH3:41])[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]4[CH2:37][C:36]([F:38])([F:39])[CH2:35]4)[C:17]4[CH2:22][CH2:21][C@H: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:40][CH3:41])[CH:6]=1

Participants

4

Reactant 1

HCID 58075483HCID 58075483, compound

Product 1

HCID 58075454HCID 58075454, compound

Reagents, catalysts & solvents 2

HCID 280Carbon DioxideSolventHCID 887MethanolSolvent2×

Procedure

A racemic mixture of N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-4-(3,3-difluoroazetidin-1-yl)-7-(4-(trifluoromethoxy)phenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine (165.2 mg, 0.279 mmol from Example 99) was purified using chiral SFC to afford 16.7 mg of peak A (Example 99A) and 17.0 mg of peak B (Example 99B). 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 20 min, absorbance 268 nm, injection 5 μL of 2 mg/mL solution in methanol (multiple stacked injections), tR (peak A)=4.9 min, tR (peak B) 15.0 min. The absolute stereochemistry of individual enantiomers (Examples 99A and 99B) was not determined LC-MS and 1H NMR analytical data for the separated enantiomers was identical to the racemate (Example 99).

Workup

  1. customwas purified
  2. customto afford 16.7 mg of peak A (Example 99A) and 17.0 mg of peak B (Example 99B)
  3. custom=4.9 min, tR (peak B) 15.0 min

Sources & evidence

ORD record
ord-a025250a6a1d4c0abf540c90076c810f
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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