4-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride → HCID 86607917, compound
Reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@:3]1([CH2:11][CH3:12])[C:7]([O:9][CH3:10])=[O:8].Cl.[CH3:14][C:15]1[CH:24]=[C:23]([CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1>>[CH2:11]([C@:3]1([C:7]([O:9][CH3:10])=[O:8])[CH2:4][CH2:5][CH2:6][C@H:2]1[NH:1][S:33]([C:30]1[CH:31]=[CH:32][C:27]([O:26][CH2:25][C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]([CH3:14])[CH:24]=2)=[CH:28][CH:29]=1)(=[O:34])=[O:35])[CH3:12]Participants
Procedure
According to the procedure of Example 53, Step 3, using methyl (1S,2R)-2-amino-1-ethylcyclopentanecarboxylate (410 mg, 1.97 mmol) and 4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl chloride hydrochloride (917 mg, 2.39 mmol), methyl (1S,2R)-1-ethyl-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylate (609 mg, 1.26 mmol, 64%) was obtained as a colorless solid after purification via column chromatography on silica gel, eluting with 30% ethyl acetate/hexanes. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 0.80-0.86 (m, 3H) 1.37-1.41 (m, 1H) 1.42-1.48 (m, 2H) 1.50-1.55 (m, 1H) 1.58-1.65 (m, 2H) 1.71-1.82 (m, 2H) 2.12 (ddd, J=12.76, 8.72, 3.54 Hz, 1H) 2.75-2.77 (m, 3H) 3.42 (td, J=9.79, 7.71 Hz, 1H) 3.69-3.71 (m, 3H) 5.57 (s, 2H) 5.64 (d, J=9.60 Hz, 1H) 7.09-7.13 (m, 2H) 7.43 (s, 1H) 7.56 (ddd, J=8.34, 7.07, 1.26 Hz, 1H) 7.74 (ddd, J=8.40, 7.01, 1.52 Hz, 1H) 7.83-7.92 (m, 3H) 8.10 (d, J=7.83 Hz, 1H).
Sources & evidence
- ORD record
- ord-4179abcd7d8b4581a894fbba25f36813
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07595327B2
Reaction notes
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