8-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic Acid → N2-(4-(Diethylamino)phenyl)-(N1,N1-dimethylglycinamide) 3,4-dihydronaphthalene-2,2(1H)-dicarboxamide
Reaction equation
CO[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([C:13]([OH:15])=O)[CH2:9][CH2:8]2.[NH2:16][CH2:17][C:18]([N:20]([CH3:22])[CH3:21])=[O:19].S(O)(O)(=O)=O.[CH2:28]([N:30]([CH2:38][CH3:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1N)[CH3:29]>O>[CH2:38]([N:30]([CH2:28][CH3:29])[C:31]1[CH:36]=[CH:35][C:34]([NH:16][CH2:17][C:18]([N:20]([CH3:22])[CH3:21])=[O:19])=[CH:33][CH:32]=1)[CH3:39].[CH2:11]1[C:12]2[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:8][CH2:9][C:10]1([C:13]([NH2:30])=[O:15])[C:18]([NH2:20])=[O:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The titled compound was prepared according to the procedure described in Example 1, substituting 2-(4-diethylamino-phenylcarbamoyl)-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid from Example 16B for 8-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid, and 2-amino-N,N-dimethyl-acetamide for N,N-diethylphenylene diamine sulfate used in Example 1. 1H NMR (300 MHz, DMSO-D6) δ 9.70 (s, 1H), 8.21 (t, J=5.4 Hz, 1H), 7.46 (t, J=9.0 Hz, 2H), 7.01–7.09 (m, 4H), 6.60 (d, J=9.0 Hz, 1H), 3.92 (d, J=5.7 Hz, 2H), 3.28 (q, J=6.9 Hz, 4H), 3.20 (d, J=17.4 Hz, 1H), 2.95 (s, 3H), 2.87 (s, 3H), 2.78 (m, 2H), 2.30 (m, 2H), and 1.05 (t, J=6.9 Hz, 6H). (one proton (ArCHaHbC(C═O)) overlapped with water)). MS (ESI) positive ion 451 (M+H)+; negative ion 449 (M−H)−.
Sources & evidence
- ORD record
- ord-a2a1ddb93eee459f9834fda66b8c29aa
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115767B2
Reaction notes
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