3-Amino-4-methoxycyclobut-3-ene-1,2-dione → 1-[3-[4-(Piperidinomethyl)pyrid-2-yloxy]prop-1-ylamino]-2-aminocyclobut-1-ene-3,4-dione

HRID 358335Notes

Reaction equation

HRID 358335 reaction equation
[NH2:1][C:2]1[C:5](=O)[C:4](=[O:7])[C:3]=1[O:8]C.[N:10]1([CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([O:23][CH2:24][CH2:25][CH2:26][NH2:27])[CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C(O)C>[N:10]1([CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([O:23][CH2:24][CH2:25][CH2:26][NH:27][C:5]3[C:4](=[O:7])[C:3](=[O:8])[C:2]=3[NH2:1])[CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 134522053-Amino-4-methoxycyclobut-3-ene-1,2-dioneHCID 146251023-({4-[(Piperidin-1-yl)methyl]pyridin-2-yl}oxy)propan-1-amine

Product 1

HCID 204486941-[3-[4-(Piperidinomethyl)pyrid-2-yloxy]prop-1-ylamino]-2-aminocyclobut-1-ene-3,4-dioneYield 64.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Amino-2-methoxy-cyclobut-1-ene-3,4-dione (0.5 g) and 3-[4-(piperidinomethyl)pyrid-2-yloxy]prop-1-ylamine (1.05 g) were refluxed in ethanol (25 ml) for 4 hours. A solid formed during the reaction. The reaction mixture was cooled and the solid collected by filtration. Recrystallisation of the solid from ethanol/methanol afforded the title product (0.88 g), m.p. 226°-8° C.

Workup

  1. customA solid formed during the reaction
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe solid collected by filtration
  4. customRecrystallisation of the solid from ethanol/methanol

Sources & evidence

ORD record
ord-7c8a971bb17f4e099da39ac23e2f3b76
Source dataset
uspto-grants-1984_08
Patent number
US04466970

Reaction notes

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