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

HRID 2354441Notes

Reaction equation

HRID 2354441 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:16][CH3:17])[CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:4][C:3]=1[F:18].[Cl:19][C:20]1[C:21]([Cl:35])=[CH:22][C:23]2[O:28][CH2:27][C:26](=[O:29])[N:25]([CH2:30][C:31]([OH:33])=O)[C:24]=2[CH:34]=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:16]([CH3:17])[C:31](=[O:33])[CH2:30][N:25]2[C:24]3[CH:34]=[C:20]([Cl:19])[C:21]([Cl:35])=[CH:22][C:23]=3[O:28][CH2:27][C:26]2=[O:29])[CH2:9][N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)=[CH:4][C:3]=1[F:18]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 574888462-(6,7-Dichloro-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)acetic acidHCID 574890531-(4-bromo-3-fluorophenyl)-N-methyl-2-(4-morpholinyl)ethanamine

Product 1

HCID 57489052N-[1-(4-bromo-3-fluorophenyl)-2-(4-morpholinyl)ethyl]-2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-N-methylacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a room temperature solution containing 1.59 g of 1-(4-bromo-3-fluorophenyl)-N-methyl-2-(4-morpholinyl)ethanamine (5.02 mmols) in 17 mL of dry DMF was added 2 g of (6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)acetic acid (7.25 mmols), 2.66 g of BOP reagent (6.02 mmols), and 1.4 mL of triethylamine (10.04 mmols). The reaction mixture was stirred at ambient temperature. After 24 h 10 mL of saturated aqueous NaHCO3 was added. The resulting precipitate was collected, washed with water, and dried in vacuo to afford an off-white solid. MS (ES) m/e 574, 576 [M+H]+.

Workup

  1. customThe resulting precipitate was collected
  2. washwashed with water
  3. customdried in vacuo
  4. customto afford an off-white solid

Sources & evidence

ORD record
ord-eded4c4a13c54b1eacd5cee2991ef51c
Source dataset
uspto-grants-2010_07
Patent number
US07749998B2

Reaction notes

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