4-Methylmorpholine → 2-(4-benzyloxy-phenyl)-N-[1-(2-dimethylamino-ethyl)-1H-indazol-6-yl]-acetamide
Reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH2:14])[CH:12]=2)[CH:7]=[N:6]1.[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31](O)=[O:32])=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl.C(N=C=NC(C)(C)CC)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C>[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:30][C:31]([NH:14][C:11]2[CH:12]=[C:13]3[C:8]([CH:7]=[N:6][N:5]3[CH2:4][CH2:3][N:2]([CH3:15])[CH3:1])=[CH:9][CH:10]=2)=[O:32])=[CH:28][CH:29]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1-(2-dimethylamino-ethyl)-1H-indazol-6-ylamine (484 mg, 2 mmol), 4-benzyloxy-phenylacetic acid (200 mg, 2 mmol), ethyldimethylpropylcarbodiimide hydrochloride (460 mg, 2.4 mmol), N-hydroxybenzotriazole (324 mg, 2.4 mmol), and N-methyl morpholine (513 mg, 4.8 mmol) in DMF (15 mL) was stirred at room temperature for 6 hours and concentrated under reduced pressure The residue was purified by flash chromatography (Silica gel, ethyl acetate/triethylamine, 30/1) to provide the title compound as a pale yellow solid (95%). 1H NMR (300 MHz, DMSO-d6) ppm 2.15 (s, 6H), 2.66 (t, J=6.44, 2H), 3.60 (s, 2H), 4.35 (t, J=6.44, 2H), 5.09 (s, 2H), 6.98 (d, J=8.82, 2H), 7.14 (m, 1H), 7.25–7.45 (m, 6H), 7.65 (m, 1H), 7.94 (m, 1H), 7.94 (s, 1H), 7.95 (s, 1H), 8.12 (s, 1H); MS (DCI/NH3) m/z 429 [M+H]+.
Workup
- concentrationconcentrated under reduced pressure The residue
- customwas purified by flash chromatography (Silica gel, ethyl acetate/triethylamine, 30/1)
Sources & evidence
- ORD record
- ord-fff2b7e8a5fd4546beaa9b700e84e723
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07071182B2
Reaction notes
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