Binap, (A+-)- → HCID 118159367, compound

HRID 713234Notes

Reaction equation

HRID 713234 reaction equation
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[N:11][C:12](Cl)=[C:13]([NH:18][CH:19]([CH3:21])[CH3:20])[N:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([CH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)(=[O:33])=[O:32].CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[N:11][C:12]([N:37]3[CH2:36][CH2:35][CH:34]([S:31]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[F:24])(=[O:33])=[O:32])[CH2:39][CH2:38]3)=[C:13]([NH:18][CH:19]([CH3:21])[CH3:20])[N:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 634876Binap, (A+-)-HCID 13825033HCID 13825033, compoundHCID 23676156Sodium t-butoxideHCID 118159187HCID 118159187, compound

Product 1

HCID 118159367HCID 118159367, compoundYield 51.5%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 6-benzyl-3-chloro-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine (117.2 mg, 0.370 mmol) and 4-((2-fluorophenyl)sulfonyl)piperidine hydrochloride (124 mg, 0.444 mmol) in toluene (1.85 mL) was treated with sodium tert-butoxide (107 mg, 1.110 mmol), BINAP (34.6 mg, 0.055 mmol), and Pd2(dba)3 (16.9 mg, 0.018 mmol). Nitrogen gas (balloon) was bubbled through the reaction mixture for 5 min. The reaction mixture was then sealed and heated at 90° C. for 18 h. The reaction mixture was opened to air and concentrated under reduced pressure. The residue was taken up in DMF/MeOH, filtered through a 0.45 μm syringe filter, and purified by HPLC Method A to give the title compound (99.7 mg, 42.3%). ESI-MS m/z [M+H]+ 523.90.

Workup

  1. customNitrogen gas (balloon) was bubbled through the reaction mixture for 5 min
  2. customThe reaction mixture was then sealed
  3. concentrationconcentrated under reduced pressure
  4. filtrationfiltered through a 0.45 μm syringe
  5. filtrationfilter
  6. custompurified by HPLC Method A

Sources & evidence

ORD record
ord-f34fb0d2fb1e491991cdac7fb135ca05
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

Loading…