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

HRID 1243139노트

반응식

HRID 1243139 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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)−.

후처리

  1. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-248e3d9c82984a7292cfeb6cee298faa
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115767B2

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