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

HRID 1243139ノート

反応式

HRID 1243139 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)−.

後処理

  1. custompurified by column chromatography

出典と根拠

ORDレコード
ord-248e3d9c82984a7292cfeb6cee298faa
出典データセット
uspto-grants-2006_10
特許番号
US07115767B2

反応ノート

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