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Diisopropylethylamine → 7-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-N-(1-(1-methyl-1H-pyrazol-4-yl)ethyl)-3-nitroquinolin-4-amine

HRID 81991
ノート
印刷プレビュー

反応式

HRID 81991 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:14]3[C:15]([CH3:20])=[N:16][O:17][C:18]=3[CH3:19])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].[CH3:24][N:25]1[CH:29]=[C:28]([CH:30]([NH2:32])[CH3:31])[CH:27]=[N:26]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.O>[CH3:20][C:15]1[C:14]([C:8]2[CH:7]=[C:6]3[C:11]([C:2]([NH:32][CH:30]([C:28]4[CH:27]=[N:26][N:25]([CH3:24])[CH:29]=4)[CH3:31])=[C:3]([N+:21]([O-:23])=[O:22])[CH:4]=[N:5]3)=[CH:10][C:9]=2[O:12][CH3:13])=[C:18]([CH3:19])[O:17][N:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 230057821-(1-methyl-1H-pyrazol-4-yl)ethan-1-amineHCID 574655804-(4-Chloro-6-methoxy-3-nitroquinolin-7-yl)-3,5-dimethylisoxazole2 回

生成物 1

HCID 709800257-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-N-(1-(1-methyl-1H-pyrazol-4-yl)ethyl)-3-nitroquinolin-4-amine収率 83%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

4-(4-Chloro-6-methoxy-3-nitroquinolin-7-yl)-3,5-dimethylisoxazole (200 mg, 0.599 mmol, for preparation see Intermediate 8) and [1-(1-methyl-1H-pyrazol-4-yl)ethyl]amine (113 mg, 0.9 mmol) were heated in a mixture of DIPEA (0.324 ml, 1.858 mmol) and NMP (15 ml) at 120° C. for 4 h. The reaction mixture was cooled to room temperature, diluted with water (300 ml) and extracted with EtOAc (2×200 ml). The combined organic phase was washed with water (300 ml) and brine (200 ml), dried with sodium sulphate and evaporated. The resulting gum was dissolved in DCM (3 ml) loaded onto a 100 g silica cartridge and eluted with 2M methanolic ammonia/DCM (0-12%). The product-containing fractions were evaporated in vacuo to give 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N-(1-(1-methyl-1H-pyrazol-4-yl)ethyl)-3-nitroquinolin-4-amine (0.21 g, 0.497 mmol, 83% yield) which was used in the subsequent step without further purification. LCMS (formate) Rt 0.87 min, MH+ 423.

後処理

  1. extractionextracted with EtOAc (2×200 ml)
  2. washThe combined organic phase was washed with water (300 ml) and brine (200 ml)
  3. dry with materialdried with sodium sulphate
  4. customevaporated
  5. dissolutionThe resulting gum was dissolved in DCM (3 ml)
  6. washeluted with 2M methanolic ammonia/DCM (0-12%)
  7. customThe product-containing fractions were evaporated in vacuo

出典と根拠

ORDレコード
ord-1983b6fd8c534a8ab0918089d9c64591
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846709B2

反応ノート

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