Triethylamine → Isobutyl 2-(((4-(diethylamino)-2-methylphenyl)amino)carbonyl)-8-methoxy-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate

HRID 1243148

반응식

HRID 1243148 반응식
[CH2:1]([O:5][C:6]([N:8](C)[C:9]1([C:21](O)=[O:22])[CH2:18][CH2:17][C:16]2[C:11](=[C:12]([O:19][CH3:20])[CH:13]=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])[CH:2]([CH3:4])[CH3:3].S(O)(O)(=O)=O.[CH2:30]([N:32]([CH2:40][CH3:41])[C:33]1[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=1)[CH3:31].[CH3:42]CN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH2:40]([N:32]([CH2:30][CH3:31])[C:33]1[CH:38]=[CH:37][C:36]([NH:39][C:21]([C:9]2([NH:8][C:6](=[O:7])[O:5][CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:18][CH2:17][C:16]3[C:11](=[C:12]([O:19][CH3:20])[CH:13]=[CH:14][CH:15]=3)[CH2:10]2)=[O:22])=[C:35]([CH3:42])[CH:34]=1)[CH3:41]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 80166N,N-Diethyl-p-phenylenediamine sulfateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 219404312-(Isobutoxycarbonyl-methyl-amino)-8-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid

생성물 1

HCID 11317633Isobutyl 2-(((4-(diethylamino)-2-methylphenyl)amino)carbonyl)-8-methoxy-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate수율 40%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The acid from Example 33F was dissolved in DMF (6.0 mL). N,N-diethyl-benzene-1,4-diamine sulfate (786 mg, 3.0 mmol), Et3N (1.0 g, 10 mmol), and TBTU (963 mg, 3.0 mmol) were added and the resulting mixture was stirred overnight and purified by column chromatography to provide the titled compound (680 mg, 40% over two steps). 1H NMR (400 MHz, DMSO-D6) δ 9.07 (s, 1H), 7.30 (d, J=8.4 Hz, 2H), 7.07 (t, J=7.6 Hz, 1H), 6.77 (d, J=8.0 Hz, 1H), 6.68 (d, J=7.2 Hz, 1H), 6.60 (d, J=8.8 Hz, 2H), 3.78 (s, 3H), 3.76 (m, 2H), 3.27 (q, J=6.8 Hz, 4H), 3.12 (d, J=17.6 Hz, 1H), 2.87 (d, J=16.0 Hz, 1H), 2.85 (s, 3H), 2.64 (m, 2H), 2.32 (m, 1H), 2.19 (m, 1H), 1.80 (m, 1H), 1.05 (t, J=6.8 Hz, 6H), and 0.85 (d, J=6.4 Hz, 6H). MS (ESI) positive ion 482 (M+H)+.

후처리

  1. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-e2d3c8b9fd874656aadaad42d3aa7149
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115767B2

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