3-Cyclobutene-1,2-dione, 3,4-dimethoxy- → HCID 18347088, compound

HRID 2269436Notes

Reaction equation

HRID 2269436 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH:17][CH2:18][CH2:19][C:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]=2)[C:10]2[CH:11]=[C:12]([NH2:16])[CH:13]=[CH:14][CH:15]=2)=[CH:5][CH:4]=1.COC1C=CC(C(NCCC2CCCCC2)C2C=C([NH2:41])C=CC=2)=CC=1.C[O:52][C:53]1[C:54](=O)[C:55](=O)[C:56]=1[O:57]C>CO>[NH2:41][C:55]1[C:56](=[O:57])[C:53](=[O:52])[C:54]=1[NH:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[NH:17][CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:11]=1

Participants

5

Reactant 3

HCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-HCID 18347056HCID 18347056, compoundHCID 18347072HCID 18347072, compound

Product 1

HCID 18347088HCID 18347088, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a similar manner to that described in Example (1c), a solution of the mixture (2.15 g) of 3-{(4-methoxyphenyl)-[2-(cyclohexen-1-yl)ethylamino]methyl}phenylamine and 3-[(4-methoxyphenyl)-(2-cyclohexylethylamino)methyl]phenylamine [prepared as described in step (b) above] in methanol (40 ml) and 3,4-dimethoxy-3-cyclobutene-1,2-dione (953 mg) were reacted, to afford a crude product, which was purified by reverse phase medium pressure chromatography using a 50:50 by volume mixture of acetonitrile and an aqueous acetic acid buffer solution (water/acetic acid/triethylamine=1000/2/2) as the eluant, to afford the title compound (815 mg) as a pale orange foamy solid.

Workup

  1. customto afford a crude product, which
  2. customwas purified by reverse phase medium pressure chromatography
  3. additionby volume mixture of acetonitrile

Sources & evidence

ORD record
ord-6947f8bb444e49c3ba3b7749173f03d8
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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