Triethylamine → N-[1-(3-bromophenyl)-2-(4-morpholinyl)ethyl]-2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-N-methylacetamide

HRID 2354343Notes

Reaction equation

HRID 2354343 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:16][CH3:17])[CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1.[Cl:18][C:19]1[C:20]([Cl:33])=[CH:21][C:22]2[O:27][CH2:26][CH2:25][N:24]([CH2:28][C:29]([OH:31])=O)[C:23]=2[CH:32]=1.CN([P+]([O:44]N1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>ClCCl.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([N:16]([CH3:17])[C:29](=[O:31])[CH2:28][N:24]2[C:23]3[CH:32]=[C:19]([Cl:18])[C:20]([Cl:33])=[CH:21][C:22]=3[O:27][CH2:26][C:25]2=[O:44])[CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57418663HCID 57418663, compoundHCID 57501274[1-(3-Bromophenyl)-2-(4-morpholinyl)ethyl]methylamine

Product 1

HCID 57457162N-[1-(3-bromophenyl)-2-(4-morpholinyl)ethyl]-2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-N-methylacetamideYield 56%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of [1-(3-bromophenyl)-2-(4-morpholinyl)ethyl]methylamine (3.06 g, 10.2 mmol) and (6,7-dichloro-2,3-dihydro-4H-1,4-benzoxazin-4-yl)acetic acid (2.82 g, 10.2 mmol) was dissolved in a mixture of dichloromethane and DMF (1:1, 100 mL). BOP Reagent (7.16 g, 16.6 mmol) was added followed by triethylamine (4.36 g, 43.2 mmol). The resultant mixture was stirred at room temperature for 16 h. The mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (150 mL) and extracted with 5% NaHCO3 (150 mL) and brine (150 mL). The organic layer was dried over MgSO4, and concentrated. The residue was recrystallized in ether, and the crystal was collected by filtration to give the title compound as a white solid (3.17 g, 56%). MS (ESI): 556.2 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  3. extractionextracted with 5% NaHCO3 (150 mL) and brine (150 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was recrystallized in ether
  7. filtrationthe crystal was collected by filtration

Sources & evidence

ORD record
ord-fcfa6cf350a945eebe1e529df8cda757
Source dataset
uspto-grants-2010_07
Patent number
US07749998B2

Reaction notes

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