Diisopropylethylamine → [4-(4-Bromo-2,5-dichloro-phenoxy)-pyridin-3-yl]-(4-cyclopropyl-3,4-dihydro-2H-quinoxalin-1-yl)-methanone

HRID 1967005Notes

Reaction equation

HRID 1967005 reaction equation
[Br:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([O:6][C:7]2[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[CH:9][CH:8]=2)=[C:4]([Cl:19])[CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH:53]1([N:56]2[C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[NH:59][CH2:58][CH2:57]2)[CH2:55][CH2:54]1>CN(C)C=O.C(OCC)(=O)C.O>[Br:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([O:6][C:7]2[CH:8]=[CH:9][N:10]=[CH:11][C:12]=2[C:13]([N:59]2[C:60]3[C:65](=[CH:64][CH:63]=[CH:62][CH:61]=3)[N:56]([CH:53]3[CH2:55][CH2:54]3)[CH2:57][CH2:58]2)=[O:15])=[C:4]([Cl:19])[CH:3]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 673204804-(4-Bromo-2,5-dichlorophenoxy)nicotinic acidHCID 673207551-Cyclopropyl-1,2,3,4-tetrahydroquinoxaline

Product 1

HCID 53312111[4-(4-Bromo-2,5-dichloro-phenoxy)-pyridin-3-yl]-(4-cyclopropyl-3,4-dihydro-2H-quinoxalin-1-yl)-methanone

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 5.0 g (13.77 mmol) 4-(4-bromo-2,5-dichloro-phenoxy)-nicotinic acid in 30 mL N,N-dimethylformamide were added 5.50 g (14.46 mmol) 0-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, commercially available, CAS RN 148893-10-1) and 7.03 mL (41.32 mmol) N,N-diisopropylethylamine. To this brown solution was added 2.52 g (14.46 mmol) 1-cyclopropyl-1,2,3,4-tetrahydro-quinoxaline (Example 8, intermediate a), the resulting clear brown solution was stirred at room temperature for 17 hours and then poured on 120 mL water and 120 mL ethyl acetate. The resulting mixture was filtered, the filter cake was thoroughly washed with water and a very small amount of ethyl acetate to give after drying 6.55 g (92%) of the title compound as a brown solid. MS (ESI): m/z=520.1 [M+H]+.

Workup

  1. filtrationThe resulting mixture was filtered
  2. washthe filter cake was thoroughly washed with water
  3. customa very small amount of ethyl acetate to give
  4. dry with materialafter drying 6.55 g (92%) of the title compound as a brown solid

Sources & evidence

ORD record
ord-d42c977e8322489e8dc93ad1b76db2ee
Source dataset
uspto-grants-2013_04
Patent number
US08420647B2

Reaction notes

Loading…