HCID 50914232, compound → HCID 58075652, compound

HRID 451167Notes

Reaction equation

HRID 451167 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:30]([CH3:32])[CH3:31])[C:17]4[CH2:23][O:22][CH2:21][CH:20]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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]([N:30]([CH3:31])[CH3:32])[C:17]4[CH2:23][O:22][CH2:21][C@H:20]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[C:18]=4[N:19]=3)=[CH:9][C:8]=2[O:33][CH3:34])[CH:6]=1

Participants

4

Reactant 1

HCID 50914232HCID 50914232, compound

Product 1

HCID 58075652HCID 58075652, 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-8-phenyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine-2,4-diamine (80.1 mg, 0.130 mmol) (Example 53) was purified using chiral SFC to afford peak A (21.2 mg, 0.044 mmol) (Example 53A) and peak B (24.2 mg, 0.051 mmol) (Example 53B). SFC Method: Chiralpak OJ-H (30×250 mm, 5 μM), 35% methanol (0.1% diethylamine) in CO2, 35° C., flow rate 70 mL/min for 13 min, absorbance 268 nm, injection 5 μL of 27 mg/mL solution in methanol (multiple stacked injections), tR (peak A)=4.5 min, tR (peak B) 9.5 min. The absolute stereochemistry of individual enantiomers (Examples 53A and 53B) was not determined LC-MS and 1H NMR analytical data for the separated enantiomers was identical to the racemate (Example 53).

Workup

  1. customwas purified
  2. customto afford peak A (21.2 mg, 0.044 mmol) (Example 53A) and peak B (24.2 mg, 0.051 mmol) (Example 53B)
  3. custom=4.5 min, tR (peak B) 9.5 min

Sources & evidence

ORD record
ord-337848c755124b18b285df46563fffd0
Source dataset
uspto-grants-2013_07
Patent number
US08486952B2

Reaction notes

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