2-Butanamine, 2-methyl- → 4-(4-Trifluoromethyl-phenyl)-3-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione

HRID 843047Notes

Reaction equation

HRID 843047 reaction equation
C(O[C:5]1[C:6](=[O:20])[C:7](=[O:19])[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)(C)C.[C:21]([NH2:26])([CH2:24][CH3:25])([CH3:23])[CH3:22]>>[F:18][C:15]([F:16])([F:17])[C:12]1[CH:11]=[CH:10][C:9]([C:8]2[C:7](=[O:19])[C:6](=[O:20])[C:5]=2[NH:26][C:21]([CH3:23])([CH3:22])[CH2:24][CH3:25])=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 689862-Butanamine, 2-methyl-HCID 120516713-Isopropoxy-4-(4-trifluoromethyl-phenyl)-cyclobut-3-ene-1,2-dione

Product 1

HCID 98397104-(4-Trifluoromethyl-phenyl)-3-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione

Procedure

In a manner similar to Example 1, Step 2, 3-isopropoxy-4-(4-trifluoromethyl-phenyl)-cyclobut-3-ene-1,2-dione (0.30 g, 1.056 mmol) and tert-amylamine (0.86 mL, 7.39 mmol) were converted to the title compound. Recrystallization from hot ethyl acetate afforded 0.250 g (76%) of compound as a tan solid: m.p. 115.4-119° C. (dec); 1H NMR (DMSO-d6) δ 8.60(br s,1H), 8.15(ABq,2H), 7.86(ABq,2H), 1.81(q,2H), 1.43(s,6H), 0.88(s,3H); IR (KBr) 3170, 2980, 1770, 1720, 1580, 1310, 1170, 1125, 1060, 1010, 850 cm−1; MS (m/z) 311 [M+].

Sources & evidence

ORD record
ord-8cc2ccc147ae440d8ff8eadd5e8e0d61
Source dataset
uspto-grants-2002_04
Patent number
US06376555B1

Reaction notes

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