Triethylamine → Methyl 2-(((4-(diethylamino)-2-methylphenyl)amino)carbonyl)-8-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate

HRID 1243139Notes

Reaction equation

HRID 1243139 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:17](O)=[O:18])[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([O:15][CH3:16])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].[CH3:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24].CN(C(O[N:35]1N=N[C:37]2[CH:38]=C[CH:40]=[CH:41][C:36]1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH2:21]([N:22]([CH2:25][CH3:26])[C:23]1[CH:38]=[CH:37][C:36]([NH:35][C:17]([C:5]2([C:3]([O:2][CH3:1])=[O:4])[CH2:14][CH2:13][C:12]3[C:7](=[C:8]([O:15][CH3:16])[CH:9]=[CH:10][CH:11]=3)[CH2:6]2)=[O:18])=[C:41]([CH3:40])[CH:24]=1)[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 695851948-methoxy-3,4-dihydro-1H-naphthalene-2,2-dicarboxylic acid methyl ester

Product 1

HCID 21940415Methyl 2-(((4-(diethylamino)-2-methylphenyl)amino)carbonyl)-8-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylateYield 41.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The crude acid from Example 12A (180 mg) was dissolved in DMF (1.5 mL) and N′,N′-diethyl-2-methyl-1,4-phenylenediamine monohydrogenchloride (150 mg, 0.7 mmol), Et3N (202 mg, 2.0 mmol), and TBTU (225 mg, 0.7 mmol) were added at ambient temperature. The mixture was stirred overnight and purified by column chromatography to provide the titled compound (120 mg, 25% over 2 steps). 1H NMR (300 MHz, DMSO-D6) δ 8.94 (s, 1H), 7.06 (t, J=7.8 Hz, 2H), 6.83 (d, J=9.0 Hz, 1H), 6.75 (d, J=8.1 Hz, 1H), 6.67 (d, J=7.8 Hz, 1H), 6.43 (m, 2H), 3.78 (s, 3H), 3.67 (s, 3H), 3.29 (q, J=6.9 Hz, 4H), 3.09 (s, 2H), 2.73 (m, 2H), 2.30 (m, 2H), 1.99 (s, 3H), and 1.05 (t, J=6.6 Hz, 6H). MS (ESI) positive ion 425 (M+H)+; negative ion 423 (M−H)−.

Workup

  1. custompurified by column chromatography

Sources & evidence

ORD record
ord-248e3d9c82984a7292cfeb6cee298faa
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

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