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

HRID 1243148Notes

Reaction equation

HRID 1243148 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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)+.

Workup

  1. custompurified by column chromatography

Sources & evidence

ORD record
ord-e2d3c8b9fd874656aadaad42d3aa7149
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

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