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

HRID 991774

Reaction equation

HRID 991774 reaction equation
C(O[C:5]1[C:6](=[O:18])[C:7](=[O:17])[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)(C)C.[NH2:19][CH:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH3:21]>C(#N)C>[CH3:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([C:8]2[C:7](=[O:17])[C:6](=[O:18])[C:5]=2[NH:19][CH:20]([CH3:21])[C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 5209072-Butanamine, 3,3-dimethyl-HCID 147378433-Isopropoxy-4-(4-methoxy-phenyl)-cyclobut-3-ene-1,2-dione

Product 1

HCID 98607093-(4-Methoxy-phenyl)-4-(1,2,2-trimethyl-propylamino)-cyclobut-3-ene-1,2-dioneYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a manner similar to Example 1, Step 2; 3-isopropoxy-4-(4-methoxy-phenyl)-cyclobut-3-ene-1,2-dione (0.300 g, 1.22 mmol) and 2-amino-3,3-dimethylbutane (0.18 mL, 1.34 mmol) in acetonitrile (7 mL) were converted to the title compound (0.28 g, 80%) m.p.: 179-181° C.; 1H NMR (DMSO-d6) δ8.56 (br d,1H), 8.06(ABq,2H), 7.09(ABq,2H), 4.31(m,1H), 3.83(s,3H), 1.24(d,3H), 0.91(s,9H); IR (KBr) 3200, 2980, 1780, 1720, 1620, 1420, 1310, 1270, 1190, 1120, 1040, 840 cm−1; MS (m/z) 287 [M+].

Sources & evidence

ORD record
ord-6690c31b4e2746dd8b67f23362e82248
Source dataset
uspto-grants-2002_10
Patent number
US06465523B1

Linked notes

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