Phosphoric Acid → HCID 17751957、化合物

HRID 1894934ノート

反応式

HRID 1894934 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[C:15]([CH2:16][CH3:17])=[C:14]([CH2:18][NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[N:21]=3)[C:13]([CH2:27][CH3:28])=[C:12]([CH2:29][NH:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([NH2:37])[N:32]=3)[C:11]=2[CH2:38][CH3:39])[CH:5]=[CH:4][CH:3]=1.CO[CH:42](OC)[CH2:43][C:44](=O)[CH3:45].OP(O)(O)=O>O>[CH3:42][C:43]1[N:37]=[C:33]2[C:34]([CH:35]=[CH:36][C:31]([NH:30][CH2:29][C:12]3[C:13]([CH2:27][CH3:28])=[C:14]([CH2:18][NH:19][C:20]4[CH:25]=[CH:24][C:23]5[C:22](=[N:26][C:4]([CH3:5])=[CH:3][CH:2]=5)[N:21]=4)[C:15]([CH2:16][CH3:17])=[C:10]([CH2:9][NH:8][C:6]4[CH:5]=[CH:4][C:3]5[C:2](=[N:1][C:11]([CH3:12])=[CH:10][CH:9]=5)[N:7]=4)[C:11]=3[CH2:38][CH3:39])=[N:32]2)=[CH:45][CH:44]=1

参加物

5

反応物 3

HCID 1004Phosphoric AcidHCID 2285484,4-Dimethoxy-2-butanoneHCID 11203277HCID 11203277、化合物

生成物 1

HCID 17751957HCID 17751957、化合物収率 23%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

1,3,5-Tris[(6-amino-pyridin-2-yl)aminomethyl]-2,4,6-triethylbenzene (2b) (4.7 g, 8.9 mmol), 4,4-dimethoxy-2-butanone (26.3 mmol), and H3PO4 (50 mL) were held at 90° for 4 h and then stirred at room temperature for 2 h. The reaction mixture was poured into water (300 mL), neutralized, and extracted several times with chloroform. The collected organic layers were dried over MgSO4 and the solvent was removed under reduced pressure. The crude product was purified several times by column chromatography (silica gel, CHCl3/CH3OH, 7:1 to 2:1 v/v). Yield 23%. M.p. 207-208° C. 1H-NMR (400 MHz, CDCl3): δ=1.23 (t, 9H, J=7.5 Hz), 2.69 (s, 9H), 2.82 (q, 6H, J=7.5 Hz), 4.74 (br s, 3H), 4.82 (d, 3H, J=3.0 Hz), 6.58 (d, 3H, J=8.6 Hz), 7.04 (d, 3H, J=8.1 Hz), 7.72 (d, 3H, J=8.6 Hz), 7.79 (d, 3H, J=8.1 Hz). 13C NMR (100 MHz, CDCl3): δ=16.9, 23.1, 25.3, 40.6, 112.1, 115.2, 118.3, 132.9, 136.2, 136.9, 144.5, 156.7, 158.4, 161.3. HR-MS calcd for C42H44N6: 674.3719; found: 674.3714. Rf=0.89 (CHCl3/CH3OH 2:1 v/v).

後処理

  1. extractionextracted several times with chloroform
  2. dry with materialThe collected organic layers were dried over MgSO4
  3. customthe solvent was removed under reduced pressure
  4. customThe crude product was purified several times by column chromatography (silica gel, CHCl3/CH3OH, 7:1 to 2:1 v/v)

出典と根拠

ORDレコード
ord-a7441e6600964c56bfcf183d99503d28
出典データセット
uspto-grants-2013_08
特許番号
US08513420B2

反応ノート

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