Triethylamine → 4-[3-(7-Hydroxy-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acid
Reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([CH2:19][O:20][C:21]3[CH:22]=[C:23]([NH:27][C:28](=[O:38])[CH2:29][C:30]([CH2:36][CH3:37])([CH2:34][CH3:35])[C:31]([OH:33])=[O:32])[CH:24]=[CH:25][CH:26]=3)=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C(N(CC)CC)C>[Pd].O1CCCC1>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([CH2:19][O:20][C:21]3[CH:22]=[C:23]([NH:27][C:28](=[O:38])[CH2:29][C:30]([CH2:36][CH3:37])([CH2:34][CH3:35])[C:31]([OH:33])=[O:32])[CH:24]=[CH:25][CH:26]=3)=[N:16]2)=[CH:11][CH:10]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture consisting of 0.37 g of 4-[3-(7-benzyloxy-2-quinolinylmethoxy)phenylamino]-2,2-diethyl-4-oxobutanoic acid (Example 18), 2 ml of triethylamine, 0.0185 g of palladium/activated carbon catalayst and 10 ml of tetrahydrofuran is hydrogenated for 3 hours under normal pressure. The reaction mixture is then filtered and concentrated by evaporation. The residue is chromatographed on silica gel using methylene chloride/methanol 95:5 and 9:1. The title compound is obtained in the form of a slightly yellowish amorphous solid; 1H-NMR, 400 MHz, DMSO, delta (ppm)=10.3 (s, 1H), 8.20 (d, 1H), 7.28 (m, 2H), 7.25 (d, 1H), 7.1-7.18 (m, 3H), 6.65 (dd, 1H), 5.22 (s, 2H), 2.47 (s, 2H), 1.49 (m, 4H), 0.78 (t, 6H).
Workup
- filtrationThe reaction mixture is then filtered
- concentrationconcentrated by evaporation
- customThe residue is chromatographed on silica gel
Sources & evidence
- ORD record
- ord-35f08e590ce341c29b3e28f2881b1bdb
- Source dataset
- uspto-grants-1996_04
- Patent number
- US05508408
Reaction notes
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