3-Butoxy-4-(1,1-dimethylpropylamino)-cyclobut-3-ene-1,2-dione → 3-{[2-(1.1-Dimethyl-propylamino)-3,4-dioxo-cyclobut-1-enylamino]-methyl}-5-methyl-benzonitrile

HRID 1956704Notes

Reaction equation

HRID 1956704 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.[C:18]([C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([CH3:28])[CH:27]=1)[CH2:23][NH2:24])#[N:19]>O1CCCC1>[CH3:15][C:11]([NH:10][C:9]1[C:8](=[O:16])[C:7](=[O:17])[C:6]=1[NH:24][CH2:23][C:22]1[CH:21]=[C:20]([CH:27]=[C:26]([CH3:28])[CH:25]=1)[C:18]#[N:19])([CH3:14])[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 158388373-Butoxy-4-(1,1-dimethylpropylamino)-cyclobut-3-ene-1,2-dioneHCID 178193443-Cyano-5-methylbenzylamine

Product 1

HCID 186636473-{[2-(1.1-Dimethyl-propylamino)-3,4-dioxo-cyclobut-1-enylamino]-methyl}-5-methyl-benzonitrileYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-butoxy-4-(1,1-dimethyl-propylamino)cyclobut-3-ene-1,2-dione (1.44 g, 6.0 mmol, Example 3) and 3-cyano-5-methylbenzylamine from Example 7, Step 3 (6.0 mmol) and tetrahydrofuran (15 mL) were stirred at room temperature for approximately 20 hours. An additional 7 mL of tetrahydrofuran were added and stirring continued for an additional 48 hours. The solvent was removed and the residue was recrystallized twice from methanol to provide 1.251 g (67%) of the title compound as a white solid: mp 231°-133° C. (softens 229° C.); 1H NMR (DMSO-d6) δ7.78 (m, 1H), 7.62 (m, 2H), 7.51 (s, 1H), 7.41 (s, br, 1H), 4.74 (d, 2H), 2.35 (s, 3H), 1.67 (m, 2H), 1.30 (s, 6H), 0.82 (m, 3H) ppm. IR (KBr): 3290, 2240, 1780, 1670 cm-1 ; MS (m/z) 311 (M+). HPLC indicates a major component (99.7%).

Workup

  1. customThe solvent was removed
  2. customthe residue was recrystallized twice from methanol

Sources & evidence

ORD record
ord-8cd870d3a4b749c99e4362d4e9071143
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

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