4-Pyridinemethanamine → 3-(1,1-Dimethylpropylamino)-4-[(pyridin-4-ylmethyl)-amino]cyclobut-3-ene-1,2-dione

HRID 362999Notes

Reaction equation

HRID 362999 reaction equation
C(O[C:6]1[C:7](=[O:17])[C:8](=[O:16])[C:9]=1[NH:10][C:11]([CH3:15])([CH3:14])[CH2:12][CH3:13])CCC.[NH2:18][CH2:19][C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1>O1CCCC1>[CH3:15][C:11]([NH:10][C:9]1[C:8](=[O:16])[C:7](=[O:17])[C:6]=1[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)([CH3:14])[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 773174-PyridinemethanamineHCID 158388373-Butoxy-4-(1,1-dimethylpropylamino)-cyclobut-3-ene-1,2-dione

Product 1

HCID 98819753-(1,1-Dimethylpropylamino)-4-[(pyridin-4-ylmethyl)-amino]cyclobut-3-ene-1,2-dioneYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the above 3-butoxy-4-(1,1-dimethylpropylamino)-cyclobut-3-ene-1,2-dione (1.197 g, 5.0 mmol) and 4-aminomethylpyridine (0.541 g) in tetrahydrofuran (10 mL) was stirred at room temperature for 23 hours. The mixture was freed of solvent and the residue was triturated with diethyl ether and dried to provide 1.154 g of a buff solid. Recrystallization (twice) of the crude product from methanol gave 0.832 g (61%) of 3-(1,1-dimethylpropylamino)-4-[(pyridin-4-ylmethyl)-amino]cyclobut-3-ene-1,2-dione as a white compound: mp 258.0°-259.5° C. dec (softens 257.5° C.); 1H NMR (DMSO-d6): δ 8.56 (m, 2H), 7.86 (m, br, 1H), 7.46 (s, br, 1H), 7.32 (m, 2H), 4.77 (d, 2H), 1.67 (q, 2H), 1.32 (s, 6H), 0.83 (t, 3H). IR (KBr): 3270, 1790, 1650 cm-1 ; MS (m/z) 273 (M+).

Workup

  1. customthe residue was triturated with diethyl ether
  2. customdried
  3. customto provide 1.154 g of a buff solid
  4. customRecrystallization (twice) of the crude product from methanol

Sources & evidence

ORD record
ord-b2a66ffc64d741f3aab5b81b772cbbe5
Source dataset
uspto-grants-1999_02
Patent number
US05872139

Reaction notes

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