Dichloromethane → (r)-7-[(4'-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid (phenyl-pyridin-2-yl-methyl)-amide

HRID 51926

反応式

HRID 51926 の反応式
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]([NH:17][C:18]3[CH:27]=[C:26]4[C:21]([CH:22]=[C:23]([C:28](O)=[O:29])[CH:24]=[N:25]4)=[CH:20][CH:19]=3)=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.Cl.CN(C)[CH2:36][CH2:37][CH2:38][N:39]=[C:40]=NCC.ON1[C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=2N=N1.[CH2:55]([N:57](CC)CC)C.Cl[CH2:63]Cl>>[C:49]1([C@@H:55]([NH:57][C:28]([C:23]2[CH:24]=[N:25][C:26]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[C:18]([NH:17][C:15]([C:10]2[C:9]([C:6]4[CH:7]=[CH:8][C:3]([C:2]([F:32])([F:31])[F:1])=[CH:4][CH:5]=4)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:16])[CH:27]=3)=[O:29])[C:38]2[CH:37]=[CH:36][CH:63]=[CH:40][N:39]=2)[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

参加物

6

反応物 5

HCID 6344Dichloromethane2 回HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 102967197-[(4'-Trifluoromethyl-biphenyl-2-carbonyl)-amino)-quinoline-3-carboxylic acid

生成物 1

HCID 10167645(r)-7-[(4'-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid (phenyl-pyridin-2-yl-methyl)-amide

実験手順

7-[(4′-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid (100 mg, 0.23 mmol) was combined with (R)-phenyl-(2-pyridyl)-methylamine (64 mg, 0.35 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (53 mg, 0.27 mmol), 1-hydroxybenzotriazole (34 mg, 0.25 mmol), and triethylamine (0.13 ml, 0.92 mmol) in 1.5 ml of dichloromethane. After stirring overnight at ambient temperature, the reaction mixture was diluted with 50 ml of dichloromethane, and the organic phase washed sequentially with water (2×20 ml), and brine, and then dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide a yellow residue. This material was purified by preparative thin-layer-chromatography on silica eluting with ethyl acetate. The product containing band was collected and eluted with 5% methanol in ethyl acetate to afford 73 mg of the title compound as a colorless solid. Optical Rotation: [α]D=−45.0° (c=0.40 mg/ml; CH3OH)

後処理

  1. washthe organic phase washed sequentially with water (2×20 ml), and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto provide a yellow residue
  6. customThis material was purified by preparative thin-layer-chromatography on silica eluting with ethyl acetate
  7. additionThe product containing band
  8. customwas collected
  9. washeluted with 5% methanol in ethyl acetate

出典と根拠

ORDレコード
ord-4c7cf59086b14ca5b87951c21d34a240
出典データセット
uspto-grants-2004_03
特許番号
US06713489B2

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