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

HRID 1243148ノート

反応式

HRID 1243148 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)+.

後処理

  1. custompurified by column chromatography

出典と根拠

ORDレコード
ord-e2d3c8b9fd874656aadaad42d3aa7149
出典データセット
uspto-grants-2006_10
特許番号
US07115767B2

反応ノート

読み込み中…