Dihydro-3,3-diethyl-2,5-furandione → 2-((5-(Benzo[d]thiazol-2-ylmethoxy)-1-(4-(pyrimidin-2-yl)benzyl)-1H-benzo[d]imidazol-2-yl)methyl)-2-ethylbutanoic acid
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH2:14])=[CH:9][CH:8]=1.F[C:16]1[CH:32]=[CH:31][C:19]([O:20][CH2:21][C:22]2[S:23][C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[N:26]=2)=[CH:18][C:17]=1[N+:33]([O-])=O.[CH2:36]([C:38]1([CH2:45][CH3:46])[CH2:42][C:41](=O)[O:40][C:39]1=[O:44])[CH3:37]>>[S:23]1[C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=[C:22]1[CH2:21][O:20][C:19]1[CH:31]=[CH:32][C:16]2[N:14]([CH2:13][C:10]3[CH:11]=[CH:12][C:7]([C:2]4[N:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[CH:8][CH:9]=3)[C:37]([CH2:36][C:38]([CH2:45][CH3:46])([CH2:42][CH3:41])[C:39]([OH:44])=[O:40])=[N:33][C:17]=2[CH:18]=1Participants
4
Procedure
The title compound was prepared using analogous conditions described in Example 208 using (4-(pyrimidin-2-yl)phenyl)methanamine and 2-((4-fluoro-3-nitrophenoxy)methyl)benzo[d]thiazole in step B and 3,3-diethyldihydrofuran-2,5-dione in step D using conventional heating. MS (ESI): mass calcd. for C33H31N5O3S, 577.71; m/z found, 578.1 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.87-8.78 (d, J=4.9, 2H), 8.43-8.36 (d, J=8.5, 2H), 8.05-7.96 (m, 2H), 7.61-7.57 (d, J=9.1, 1H), 7.57-7.51 (ddd, J=8.4, 7.2, 1.2, 1H), 7.48-7.42 (m, 2H), 7.39-7.35 (m, 1H), 7.35-7.32 (d, J=8.3, 2H), 7.30-7.24 (dd, J=9.1, 2.4, 1H), 5.89-5.76 (s, 2H), 5.70-5.61 (s, 2H), 3.40-3.37 (s, 2H), 1.92-1.71 (m, 4H), 0.93-0.82 (t, J=7.4, 6H).
Sources & evidence
- ORD record
- ord-915121d29393449bb3da813fe46f37c4
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067917B2
Reaction notes
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