Phosphoric Acid → HCID 17751957, compound

HRID 1894934Notes

Reaction equation

HRID 1894934 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 17751957HCID 17751957, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-a7441e6600964c56bfcf183d99503d28
Source dataset
uspto-grants-2013_08
Patent number
US08513420B2

Reaction notes

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