Ammonia → 2-Cyclohexyl-2-[4-(quinolin-2-yl-methoxy)phenyl]acetic acid N-hydroxy-N-methyl-amide
Reaction equation
[CH:1]1([CH:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)=[CH:13][CH:12]=2)[C:8](O)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C(C2C=CC(OCC3C=CC4C(=CC=CC=4)N=3)=CC=2)C(O)=O)CCCC1.C1C2C(=CC=CC=2)C=CC=1COC1C=C(C([O:84][N:85]=[CH:86]C(O)=O)CCCC2C=CC=CC=2)C=CC=1.N>>[OH:84][N:85]([CH3:86])[C:8](=[O:9])[CH:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)=[CH:13][CH:12]=1Participants
Reactant 4
Product 1
Procedure
The desired material was prepared according to the procedures described in Example 4 substituting 2-cyclohexyl-2-[4-(quinolin-2-yl-methoxy)phenyl]acetic acid for 2-cyclopentyl-2-[4-(quinolin-2-yl-methoxy)phenyl]acetic acid and Example 6 substituting 2-cyclohexyl-2-[4-(quinolin-2-yl-methoxy)phenyl]acetic acid for {[1-(3-[2-naphthylmethoxy]-phenyl)-4-phenylbutyl]oximino}acetic acid. 1H NMR (DMSO-d6, 300 MHz) δ 0.7 (m, 1H), 1.0 (m, 1H), 1.15 (m, 4H), 1.55(m, 2H), 1.65 (m, 2H), 1.85 (m, 1H), 3.03 (s, 3H), 3.86 (d, 1H, J=7Hz), 4.84 (s, 2H), 7.0 (d, 2H, J=7Hz), 7.2 (d, 2H, J=7Hz), 7.62 (d-t, 1H, J=8Hz and 2Hz),7.68 (d, J=8Hz, 1H), 7.8 (dt, J=8Hz, 2Hz, 1H,), 8.0 (t, J=8Hz, 2H), 8.43 (d, J=8Hz, 1H), 9.8 (s, 1H). IR (CDCl3):3520, 1610 cm-1. MS (DCI/NH3) m/e 405 (M+H)+. Analysis calcd for C25H28N2O3 : C, 74.23; H, 6.98; N, 6.93. Found: C, 73.96; H, 7.04; N, 6.74.
Sources & evidence
- ORD record
- ord-08f2170268b84bab9f86ff3ea2b4be25
- Source dataset
- uspto-grants-1994_10
- Patent number
- US05358955
Reaction notes
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