HCID 118348002, compound → HCID 178461043, compound
Reaction equation
CC1(C)C(C)(C)OB(C2C=CC([C:15]3[N:16]=[C:17]([C@@H:20]4[CH2:24][CH2:23][CH2:22][N:21]4[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[NH:18][CH:19]=3)=CC=2)O1.[CH2:33]([S:36]([N:39]1[CH2:44][CH2:43][N:42]([CH2:45][C:46]2[CH:51]=[CH:50][C:49]([NH:52][C:53]([C:55]3[CH:60]=[CH:59][C:58]([C:61]4[CH:66]=[CH:65][C:64](C(NC5C=CC(CN6CCN(S(CCC)(=O)=O)CC6)=CC=5)=O)=[CH:63][CH:62]=4)=[CH:57][CH:56]=3)=[O:54])=[CH:48][CH:47]=2)[CH2:41][CH2:40]1)(=[O:38])=[O:37])[CH2:34][CH3:35]>>[CH2:33]([S:36]([N:39]1[CH2:44][CH2:43][N:42]([CH2:45][C:46]2[CH:47]=[CH:48][C:49]([NH:52][C:53]([C:55]3[CH:56]=[CH:57][C:58]([C:61]4[CH:62]=[CH:63][C:64]([C:15]5[N:16]=[C:17]([C@@H:20]6[CH2:24][CH2:23][CH2:22][N:21]6[C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[NH:18][CH:19]=5)=[CH:65][CH:66]=4)=[CH:59][CH:60]=3)=[O:54])=[CH:50][CH:51]=2)[CH2:41][CH2:40]1)(=[O:37])=[O:38])[CH2:34][CH3:35]Participants
3
Procedure
The title compound is prepared from 5 (above) and (S)-tert-butyl 2-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (Syngene) using the Suzuki-Miyaura cross-coupling procedure outlined above for the preparation of (7). Yield: 156.9 mg (66%). HPLC: tR 1.88 min (method 1); tR 2.28 min, 96.6% purity (method 2). LC-MS m/z calcd for C39H48N6O5S ([M]+), 712. found, 713 ([M+H]+). 1H NMR (CDCl3): δ 1.06 (t, J=7.0 Hz, 3H), 1.51 (s, 9H), 1.86 (m, 2H), 1.98 (m, 1H), 2.17 (m, 2H), 2.53 (m, 4H), 2.88 (m, 2H), 3.07 (m, 1H), 3.29 (m, 4H), 3.43 (m, 2H), 3.53 (s, 2H), 4.98 (m, 1H), 7.28 (br, 1H), 7.32 (m, 2H), 7.56 (br, 1H), 7.63 (m, 2H), 7.73 (m, 2H), 7.87 (m, 2H), 7.93 (m, 2H).
Sources & evidence
- ORD record
- ord-f68928432ad542c89afbc2f93185e3a7
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09125904B1
Reaction notes
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