Reaction equation
CC1(C)C[CH:10]([NH2:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7]C=2)[O:3]1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([CH3:25])=[C:19]2[CH2:26][C:27]([OH:29])=O.CCN=C=NCCCN(C)C.[ClH:41].[CH:42]1[CH:43]=[CH:44][C:45]2N(O)N=N[C:46]=2[CH:47]=1.C(N(CC)CC)C>ClCCl>[Cl:41][C:42]1[CH:47]=[C:46]2[C:45](=[CH:44][CH:43]=1)[O:3][C:4]1([CH2:5][CH2:6][CH2:7]1)[CH2:9][CH:10]2[NH:12][C:27](=[O:29])[CH2:26][C:19]1[C:18]2[C:22](=[CH:23][CH:24]=[C:16]([O:15][CH3:14])[CH:17]=2)[NH:21][C:20]=1[CH3:25]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
The title compound was prepared from Intermediate 2 (200 mg, 0.896 mmol) and (5-methoxy-2-methyl-1H-indol-3-yl)acetic acid (195 mg, 0.896 mmol) in presence of EDCI.HCl (256 mg, 1.345 mmol), HOBt (205 mg, 1.345 mmol) and triethylamine (374 μl, 3.003 mmol) in dichloromethane (10 ml) as described in Example 1 to give 35 mg of the product as a white solid; IR (KBr) 3383, 2934, 2343, 1648, 1475, 1217, 820 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.50-1.65 (m, 5H), 1.83-1.95 (m, 3H), 2.40 (s, 3H), 3.73 (s, 3H), 3.82 (s, 2H), 5.23 (q, J=9.6 Hz, 1H), 5.76 (d, J=8.7 Hz, 1H), 6.62 (d, J=8.4 Hz, 1H), 6.77 (dd, J=2.4, 6.6 Hz, 1H), 6.82-6.89 (m, 2H), 6.98 (dd, J=2.1, 6.3 Hz, 1H), 7.14 (d, J=8.4 Hz, 1H), 7.84 (s, 1H); ESI-MS (m/z) 423.58 (M−H)−.
Sources & evidence
- ORD record
- ord-d5baacfe4c6e4c708efa07ca1ad92164
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08487121B2
Linked notes
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