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Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → 4-[(3,4-Dimethoxy-phenylamino)-methyl]-N-(3-thiophen-2-yl-phenyl)-benzamide

HRID 252808
ノート
印刷プレビュー

反応式

HRID 252808 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([NH:23][CH2:24][C:25]2[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([NH:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:29]([NH:12][C:8]3[CH:9]=[CH:10][CH:11]=[C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)[CH:7]=3)=[O:30])=[CH:32][CH:33]=2)[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27946813-(Thiophen-2-yl)anilineHCID 224788804-[(3,4-Dimethoxyphenylamino)-methyl]-benzoic Acid

生成物 1

HCID 597367084-[(3,4-Dimethoxy-phenylamino)-methyl]-N-(3-thiophen-2-yl-phenyl)-benzamide収率 25%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

To a stirred solution of 31 (122 mg, 0.696 mmol), acid 4 (182 mg, 0.633 mmol) and BOP (308 mg, 0.696 mmol) in DMF (4 ml) was added B3N (265 μl, 1.90 mmol). The reaction was stirred 3 h at room temperature under nitrogen, quenched with H2O and evaporated. The residue was extracted with ethyl acetate, washed with saturated solutions of NH4Cl, NaHCO3 and brine. The organic layer was dried over anhydrous MgSO4 and concentrated in vacuum to form a material which was purified by flash chromatography (eluent 40% EtOAc in hexane) to give the title compound 32 (70 mg, 25%) as a yellow solid. 1H NMR: (DMSO) δ (ppm): 10.25 (s, 1H), 8.09-8.08 (m, 1H), 7.73 (ddd, J=7.6, 3.7, 3.7 Hz, 1H), 7.54 (dd, J=5.1, 1.0 Hz, 1H), 7.49 (d, J=8.2 Hz, 2H), 7.45 (dd, J=3.7, 1.2 Hz, 1H), 7.42-7.32 (m, 2H), 7.13 (dd, J=5.1, 3.7 Hz, 1H), 6.64 (d, J=8.6 Hz, 1H), 6.31 (d, J=2.5 Hz, 1H), 6.00-5.97 (m, 2H), 4.31 (d, J=6.1 Hz, 2H), 3.65 (s, 3H), 3.59 (s, 3H). MS: (calc), 444.2; (obt.) 445.5 (MH)+.

後処理

  1. customquenched with H2O
  2. customevaporated
  3. extractionThe residue was extracted with ethyl acetate
  4. washwashed with saturated solutions of NH4Cl, NaHCO3 and brine
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. concentrationconcentrated in vacuum
  7. customto form a material which
  8. customwas purified by flash chromatography (eluent 40% EtOAc in hexane)

出典と根拠

ORDレコード
ord-82ab630b17974cfcb0a795923e7e19f6
出典データセット
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07868205B2

反応ノート

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