Benzenamine, 4-(4-morpholinyl)- → HCID 86587185, compound

HRID 2414508Notes

Reaction equation

HRID 2414508 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:16][CH3:17])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9]([C:12]([OH:14])=O)=[CH:8][C:7]2=[O:15].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[O:50]1[CH2:55][CH2:54][N:53]([C:56]2[CH:62]=[CH:61][C:59]([NH2:60])=[CH:58][CH:57]=2)[CH2:52][CH2:51]1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[N:53]1([C:56]2[CH:57]=[CH:58][C:59]([NH:60][C:12]([C:9]3[NH:10][C:11]4[C:6]([C:7](=[O:15])[CH:8]=3)=[CH:5][C:4]([O:16][CH3:17])=[CH:3][C:2]=4[Br:1])=[O:14])=[CH:61][CH:62]=2)[CH2:52][CH2:51][O:50][CH2:55][CH2:54]1

Participants

7

Reactant 5

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22142213HCID 22142213, compound

Product 1

HCID 86587185HCID 86587185, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a yellow suspension of 8-bromo-6-methoxy-4-oxo-1,4-dihydroquinoline-2-carboxylic acid (Reference Example 27a) (3.446 g, 11.56 mmol), TBTU (9.039 g, 28.15 mmol), and HOBT (3.757 g, 27.8 mmol) in 100 mL dimethylformamide was added 4-morpholinoaniline (2.733 g, 15.3 mmol) and diisopropylethyl amine (8.2 mL, 50.2 mmol). The resulting maroon solution was stirred at room temperature under nitrogen for 16 hours during which time the reaction became greenish brown and formed a large amount of precipitate. The reaction mixture was filtered and the solids washed with dimethylformamide, water, and methanol. Drying under high vacuum afforded the desired product as a yellow solid (3.09 g, 58%). 1H NMR (300 MHz, DMSO, d6) δ 12.13 (s, 1H, NH), 10.18 (s, 1H, C(O)NH), 7.90 (d, 1H, Jm=2.7 Hz, ArH5), 7.68 (d, 2H, Jo=9.0 Hz, ArH2′ & H6′), 7.63 (s, 1H, C═CH), 7.51 (d, 1H, Jm=2.7 Hz, ArH7), 7.00 (d, 2H, Jo=9.0 Hz, ArH3′ & H5′), 3.94 (s, 3H, OCH3), 3.75 (t, 4H, J=4.8 Hz, OCH2CH2N), 3.10 (t, 4H, J=4.8 Hz, OCH2CH2N); Mass Spec.: calc. for [C21H20BrN3O4+H]+ Theor. m/z=458, 460; Obs.=458, 460.

Workup

  1. customformed a large amount of precipitate
  2. filtrationThe reaction mixture was filtered
  3. washthe solids washed with dimethylformamide, water, and methanol
  4. customDrying under high vacuum

Sources & evidence

ORD record
ord-a57c0c96938e4bf98e6920e2a49eec66
Source dataset
uspto-grants-2004_11
Patent number
US06812225B2

Reaction notes

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