Diisopropylethylamine → 1-(5-tert-Butyl-2-m-tolyl-2H-pyrazol-3-yl)-3-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-urea

HRID 1029193ノート

反応式

HRID 1029193 の反応式
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:16]=[CH:15][N:14]=[C:13]3[C:8]=2[C:9]2[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=2[C:11](=[O:17])[NH:12]3)=[CH:4][CH:3]=1.ClC(Cl)(Cl)C[O:27][C:28](=O)[NH:29][C:30]1[N:31]([C:39]2[CH:40]=[C:41]([CH3:45])[CH:42]=[CH:43][CH:44]=2)[N:32]=[C:33]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH:34]=1.CCN(C(C)C)C(C)C>CS(C)=O.O.CCOC(C)=O>[C:35]([C:33]1[CH:34]=[C:30]([NH:29][C:28]([NH:1][C:2]2[CH:23]=[CH:22][C:5]([O:6][C:7]3[CH:16]=[CH:15][N:14]=[C:13]4[C:8]=3[C:9]3[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=3[C:11](=[O:17])[NH:12]4)=[CH:4][CH:3]=2)=[O:27])[N:31]([C:39]2[CH:40]=[C:41]([CH3:45])[CH:42]=[CH:43][CH:44]=2)[N:32]=1)([CH3:38])([CH3:36])[CH3:37]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 44598708(5-tert-butyl-2-m-tolyl-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl esterHCID 581683671-(4-Amino-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-one

生成物 1

HCID 581681131-(5-tert-Butyl-2-m-tolyl-2H-pyrazol-3-yl)-3-[4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-urea収率 24.6%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 22728543Water ethylacetate溶媒

反応条件

温度
60 °C

実験手順

Compound 137 (50 mg, 0.16 mmol), (5-tert-butyl-2-m-tolyl-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (80 mg, 0.20 mmol), and DIEA (0.08 mL, 0.49 mmol) were suspended in DMSO (2 mL), and stirred overnight at 60° C. The reaction solution was diluted with H2O/EtOAc, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude product was purified via Biotage eluting with a gradient of 25 to 100% EtOAc in hexanes to provide 230 (22 mg, 24% yield) as a tan solid. LC-MS (M+H=559, obsd.=559).

後処理

  1. filtrationfiltered through an Extrelut column
  2. washThe column was washed with EtOAc
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified via Biotage
  5. washeluting with a gradient of 25 to 100% EtOAc in hexanes

出典と根拠

ORDレコード
ord-7611a6ea622f406a99ad5d5f8f59f140
出典データセット
uspto-grants-2014_05
特許番号
US08735584B2

反応ノート

読み込み中…