Benzenamine, 4-(4-morpholinyl)- → 6-Methoxy-8-(4-methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

HRID 2414519ノート

反応式

HRID 2414519 の反応式
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)[CH:13]=1)[O:10][C:9]([C:21]([OH:23])=O)=[CH:8][C:7]2=[O:24].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.ON1C2C=CC=CC=2N=N1.[N:57]1([C:63]2[CH:69]=[CH:68][C:66]([NH2:67])=[CH:65][CH:64]=2)[CH2:62][CH2:61][O:60][CH2:59][CH2:58]1>CN(C)C1C=CN=CC=1.CN(C)C=O.C(N(CC)CC)C>[N:57]1([C:63]2[CH:64]=[CH:65][C:66]([NH:67][C:21]([C:9]3[O:10][C:11]4[C:6]([C:7](=[O:24])[CH:8]=3)=[CH:5][C:4]([O:3][CH3:2])=[CH:13][C:12]=4[N:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]3)=[O:23])=[CH:68][CH:69]=2)[CH2:58][CH2:59][O:60][CH2:61][CH2:62]1

参加物

8

反応物 4

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 757711-HydroxybenzotriazoleHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 692667556-Methoxy-8-(4-Methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid hydrochloride

生成物 1

HCID 235333236-Methoxy-8-(4-methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

6-Methoxy-8-(4-Methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid hydrochloride (Reference Example 2) (3.0 g, 8.5 mmol), TBTU (5.5 g, 17 mmol), 1-hydroxybenztriazole (2.6 g, 17 mmol), 4-dimethylaminopyridine (0.05 g, catalytic) and commercially available 4-morpholin-4-yl-aniline (1.66 g, 9.3 mmol) were dissolved in dimethylformamide (100 mL). Triethylamine (3.5 mL, 25 mmol was added and this mixture stirred at room temperature for 17 hours. The reaction mixture was concentrated under vacuum and the residue was partitioned between chloroform (400 mL) and saturated aqueous sodium bicarbonate (50 mL). The organic′layer was separated, dried (Na2SO4), vacuum-filtered and concentrated under vacuum. The residue was purified by chromatography on silica eluted with 2-5% methanol in chloroform and then triturated with ether to yield a yellow powder. (1.6 g=39%) LCMS-m/z=479.5 mp=234-236° C.

後処理

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was partitioned between chloroform (400 mL) and saturated aqueous sodium bicarbonate (50 mL)
  3. customThe organic′layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationvacuum-filtered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by chromatography on silica
  8. washeluted with 2-5% methanol in chloroform
  9. customtriturated with ether
  10. customto yield a yellow powder

出典と根拠

ORDレコード
ord-6265a0a0aa114d00a65d1a27f7f585d8
出典データセット
uspto-grants-2004_11
特許番号
US06812225B2

反応ノート

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