Water → HCID 136078962, compound

HRID 1409285Notes

Reaction equation

HRID 1409285 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C@H:9]1[N:14]2[N:15]=[CH:16][N:17]=[C:13]2[NH:12][C@@H:11]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:10]1.O>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C@H:9]1[N:14]2[N:15]=[CH:16][N:17]=[C:13]2[NH:12][C@@H:11]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:10]1.[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C@@H:9]1[N:14]2[N:15]=[CH:16][N:17]=[C:13]2[NH:12][C@H:11]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:10]1

Participants

5

Reactant 2

HCID 962WaterHCID 136078962HCID 136078962, compound

Product 2

HCID 136078962HCID 136078962, compoundHCID 136078963HCID 136078963, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Chiral resolution of cis-7-(2-Chloro-6-fluorophenyl)-5-(4-chlorophenyl)-4,5,6,7-tetrahydro-[1,2,4]triazolo[1,5-a]pyrimidine: Chiral resolution of 7-(2-Chloro-6-fluorophenyl)-5-(4-chlorophenyl)-4,5,6,7-tetrahydro[1,2,4]triazolo[1,5a]pyrimidine was carried out on the Waters 2695 HPLC instrument, equipped with CHIRALPAK® AD-RH column. Eluent system was: 30% A (H2O), 70% B (EtOH); flow rate=0.5 mL/min; λ=219 nm. The two enantiomers, 40a, (R,S)-7-(2-Chloro-6-fluoro-phenyl)-5-(4-chloro-phenyl)-4,5,6,7-tetrahydro-[1,2,4]triazolo[1,5-a]pyrimidine, and 40b, (S,R)-7-(2-Chloro-6-fluoro-phenyl)-5-(4-chloro-phenyl)-4,5,6,7-tetrahydro-[1,2,4]triazolo[1,5-a]pyrimidine were isolated by removal of the solvents from peaks eluted at 43.5 minutes and 57.8 minutes respectively. 40a, (R,S)-7-(2-Chloro-6-fluoro-phenyl)-5-(4-chloro-phenyl)-4,5,6,7-tetrahydro-[1,2,4]triazolo[1,5-a]pyrimidine: Rf=0.16 (EtOAc/Hexanes 33.3:66.7). MS: MH+=363. 1H NMR (500 MHz, DMSO-d6): δ 7.54-7.15 (m, 8H, CHar), 5.98-5.94 (m, 1H, CH), 4.82-4.78 (m, 1H, CH), 2.47-2.13 (m, 2H, CH2). HPLC: 99.8% (Method A, tR=3.67 min), CHIRALPAK® AD-RH column Rf=43.5 minutes. 40b, (S,R)-7-(2-Chloro-6-fluoro-phenyl)-5-(4-chloro-phenyl)-4,5,6,7-tetrahydro-[1,2,4]triazolo[1,5-a]pyrimidine: Rf=0.16 (EtOAc/Hexanes 33.3:66.7). MS: MH+=363. 1H NMR (500 MHz, DMSO-d6): δ 7.54-7.15 (m, 8H, CHar), 5.98-5.94 (m, 1H, CH), 4.82-4.78 (m, 1H, CH), 2.47-2.13 (m, 2H, CH2). HPLC: 99.8% (Method A, tR=3.67 min), CHIRALPAK® AD-RH column Rf=57.8 minutes.

Workup

  1. customequipped with CHIRALPAK® AD-RH column

Sources & evidence

ORD record
ord-6d333a079009477eaa11c61a8d0e18d1
Source dataset
uspto-grants-2014_12
Patent number
US08921381B2

Reaction notes

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