Phosphoric Acid → HCID 17751957, 화합물

HRID 1894934노트

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HRID 1894934 반응식
[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

참가 물질

5

반응물 3

HCID 1004Phosphoric AcidHCID 2285484,4-Dimethoxy-2-butanoneHCID 11203277HCID 11203277, 화합물

생성물 1

HCID 17751957HCID 17751957, 화합물수율 23%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a7441e6600964c56bfcf183d99503d28
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513420B2

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