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Aniline → N1-(3-Fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-N3-phenylmalonamide

HRID 2117083
ノート
印刷プレビュー

反応式

HRID 2117083 の反応式
[F:1][C:2]1[CH:3]=[C:4]([NH:18][C:19](=[O:24])[CH2:20][C:21]([OH:23])=O)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:14]2=[CH:15][CH:16]=[CH:17][N:13]2[N:12]=[CH:11][N:10]=1.CN([P+](O[N:36]1N=N[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.NC1C=CC=CC=1>CN(C)C=O.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([NH:18][C:19](=[O:24])[CH2:20][C:21]([NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:23])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:14]2=[CH:15][CH:16]=[CH:17][N:13]2[N:12]=[CH:11][N:10]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6115AnilineHCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 210815903-(3-Fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenylamino)-3-oxopropanoic acid

生成物 1

HCID 11668583N1-(3-Fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-N3-phenylmalonamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 3-(3-fluoro-4-(pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenylamino)-3-oxopropanoic acid (17 mg, 0.052 mmol), BOP reagent (34 mg, 0.077 mmol), 4-methylmorpholine (28 μL, 0.26 mmol), and aniline (4.7 μL, 0.052 mmol) in dimethylformamide (0.5 mL) was stirred at room temperature for 16 h. The reaction was diluted with EtOAc (4 mL) and washed with water, 10% aq LiCl solution, and brine (1×3 mL each). The organic solution was dried over anhydrous Na2SO4 and then concentrated in vacuo. Purification by flash chromatography on silica gel (SiO2, EtOAc/Hexane 7:3) gave the desired compound as a white solid. The product was lyophilized with acetonitrile/water to give the title compound (12 mg, 57%) as a white powder. 1H NMR (CDCl3) δ 9.23 (br s, 1H), 8.22 (br s, 1H), 7.90 (s, 1H), 7.72 (m, 1H), 7.46 (d, 1H, J=8.2 Hz), 7.20 (m, 7H), 6.95 (m, 1H), 6.78 (m, 1H), 3.47 (s, 2H); MS(ESI+) m/z 406.1 (M+H)+.

後処理

  1. washwashed with water, 10% aq LiCl solution, and brine (1×3 mL each)
  2. dry with materialThe organic solution was dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography on silica gel (SiO2, EtOAc/Hexane 7:3)

出典と根拠

ORDレコード
ord-e9a224c3f98044b59967e32a04239aba
出典データセット
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07439246B2

反応ノート

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