4-(Aminomethyl)-3-chlorobenzonitrile → 3-Chloro-4-{[3,4-dioxo-2-(1,2,2-trimethyl-propylamino)-cyclobut-1-enylamino]-methyl}-benzonitrile

HRID 1956702Notes

Reaction equation

HRID 1956702 reaction equation
C(O[C:6]1[C:7](=[O:18])[C:8](=[O:17])[C:9]=1[NH:10][CH:11]([CH3:16])[C:12]([CH3:15])([CH3:14])[CH3:13])CCC.[Cl:19][C:20]1[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[CH:24][C:21]=1[CH2:22][NH2:23]>O1CCCC1>[Cl:19][C:20]1[CH:27]=[C:26]([CH:25]=[CH:24][C:21]=1[CH2:22][NH:23][C:6]1[C:7](=[O:18])[C:8](=[O:17])[C:9]=1[NH:10][CH:11]([CH3:16])[C:12]([CH3:13])([CH3:14])[CH3:15])[C:28]#[N:29]

Participants

4

Reactant 2

HCID 40897884-(Aminomethyl)-3-chlorobenzonitrileHCID 541350113-Butoxy-4-(1,2,2-trimethyl-propylamino)-cyclobut-3-ene-1,2-dione

Product 1

HCID 178193043-Chloro-4-{[3,4-dioxo-2-(1,2,2-trimethyl-propylamino)-cyclobut-1-enylamino]-methyl}-benzonitrileYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-butoxy-4-(1,2,2-trimethyl-propylamino)cyclobut-3-ene-1,2-dione (1.27 g, 5.0 mmol, Example 5), 2-chloro-4-cyanobenzylamine (0.833 g, 5.0 mmol, Example 2, Step 3) and tetrahydrofuran (8 mL) was stirred at room temperature for 23 hours, refluxed for 4 hours and allowed to stand at room temperature for approximately 62 hours. The mixture was freed of solvent and the residue was triturated with diethyl ether and dried. The resulting white solid (1.096 g) was recrystallized three times from methanol to yield 771 mg (45%) of the title compound as a faintly pink solid: mp 250.0°-251.5° C. (softens 248.0° C.); 1H NMR (DMSO-d6) δ8.10 (d, 1H), 7.88 (m, 1H), 7.70 (br m, 1H), 7.61 (d, 1H), 7.37 (br m, 1H), 4.88 (m, 1H), 3.91 (br m, 1H), 1.11 (d, 3H), 0.86 (s, 9H) ppm IR (KBr): 3200, 2230, 1790, 1635 cm-1 ; MS (m/z) 345/347 (M+). HPLC indicates a major component (98.7%).

Workup

  1. temperaturerefluxed for 4 hours
  2. customthe residue was triturated with diethyl ether
  3. customdried
  4. customThe resulting white solid (1.096 g) was recrystallized three times from methanol

Sources & evidence

ORD record
ord-a403d13d529d4b3c8d558a8d62afb912
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

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