HCID 58075598, compound → HCID 58075797, compound

HRID 475918Notes

Reaction equation

HRID 475918 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:23]=[C:22]([N:24]([CH3:26])[CH3:25])[C:21]4[CH2:20][CH2:19][CH2:18][CH:17]([C:27]5[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=5)[C:16]=4[N:15]=3)=[CH:9][C:8]=2[O:34][CH3:35])[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:23]=[C:22]([N:24]([CH3:26])[CH3:25])[C:21]4[CH2:20][CH2:19][CH2:18][C@H:17]([C:27]5[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=5)[C:16]=4[N:15]=3)=[CH:9][C:8]=2[O:34][CH3:35])[CH:6]=1

Participants

4

Reactant 1

HCID 58075598HCID 58075598, compound

Product 1

HCID 58075797HCID 58075797, compound

Reagents, catalysts & solvents 2

HCID 280Carbon DioxideSolventHCID 887MethanolSolvent2×

Procedure

A racemic mixture of N2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-8-(4-fluorophenyl)-N4,N4-dimethyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine (Example 127) was purified using chiral SFC to afford peak A (Example 127A) and peak B (Example 127B). 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 13 min, absorbance 268 nm, injection 5 μL of 2 mg/mL solution in methanol (multiple stacked injections), tR (peak A)=4.3 min, tR (peak B) 9.6 min. The absolute stereochemistry of individual enantiomers (Examples 7 and 8) was not determined LC-MS and 1H NMR analytical data for the separated enantiomers was identical to the racemate (Example 127).

Workup

  1. customwas purified
  2. customto afford peak A (Example 127A) and peak B (Example 127B)
  3. custom=4.3 min, tR (peak B) 9.6 min

Sources & evidence

ORD record
ord-9265d0a940d747d1b37cc0799b127c58
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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