Nitrogen → HCID 59785711、化合物

HRID 383594

反応式

HRID 383594 の反応式
N#N.CCN(CC)CC.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH2:22][C:23]([OH:25])=O)[CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19].[CH3:26][O:27][C:28]([C:30]1[CH:34]=[C:33]([C:35]2[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][C:36]=2[N+:42]([O-:44])=[O:43])[O:32][C:31]=1[CH3:45])=[O:29]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:26][O:27][C:28]([C:30]1[CH:34]=[C:33]([C:35]2[CH:40]=[CH:39][C:38]([NH:41][C:23](=[O:25])[CH2:22][C:14]3[CH:15]=[C:16]([O:20][CH3:21])[C:17]([O:18][CH3:19])=[C:12]([O:11][CH3:10])[CH:13]=3)=[CH:37][C:36]=2[N+:42]([O-:44])=[O:43])[O:32][C:31]=1[CH3:45])=[O:29]

参加物

7

反応物 4

HCID 947NitrogenHCID 8471TriethylamineHCID 703723,4,5-Trimethoxyphenylacetic acidHCID 59785713HCID 59785713、化合物

生成物 1

HCID 59785711HCID 59785711、化合物収率 55%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

(The following reaction is done in an anhydrous N2 atmosphere.) Suspend EDCHCl (138 mg, 0.72 mmol) and Et3N (101 μL, 0.72) in anhydrous DCM (4.5 mL) and stir the resulting solution for 5 min at rt. Add 2-(3,4,5-Trimethoxy-phenyl)-acetic acid (163 mg, 0.72 mmol) and DMAP (8 mg, 0.07 mmol) and stir the resulting solution for 10 min. Add 5-(4-Amino-2-nitro-phenyl)-2-methyl-furan-3-carboxylic acid methyl ester (58) (100 mg, 0.36 mmol) and stir the reaction solution for 22 h at rt. Quench reaction solution with sat. aqu. NH4Cl and water, separate layers and extract aqu. layer with DCM (3 times). Wash the combined organic layer with water and brine and dry with Na2SO4. Purify the crude product by preparative radial chromatography (silica gel, EtOAc/CyH 1+1) to obtain 2-Methyl-5-{2-nitro-4-[2-(3,4,5-trimethoxy-phenyl)-acetylamino]-phenyl}-furan-3-carboxylic acid methyl ester (59) (96 mg, 55%) as an yellow solid. 1H NMR (400 MHz, CDCl3): 2.55 (s, 3H); 3.65 (s, 2H); 3.79 (s, 3H); 3.81 (s, 6H); 3.82 (s, 3H); 6.50 (s, 2H); 6.77 (s, 1H); 7.53 (d, 1H, J=8.6 Hz); 7.66 (dd, 1H, J1=8.6 Hz, J2=2.0 Hz); 7.93 (br.s, 1 H); 7.96 (d, 1H, J=2.0 Hz).

後処理

  1. custom(The following reaction
  2. customQuench
  3. customreaction solution with sat. aqu
  4. customNH4Cl and water, separate layers
  5. extractionextract aqu
  6. washWash the combined organic layer with water and brine
  7. dry with materialdry with Na2SO4
  8. customPurify the crude product by preparative radial chromatography (silica gel, EtOAc/CyH 1+1)

出典と根拠

ORDレコード
ord-4493adfda4d44c42b794de79a737ba07
出典データセット
uspto-grants-2013_02
特許番号
US08367677B2

関連ノート

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