Hexahydrophthalic anhydride, cis- → racemic cis-2-(5-(Benzo[d]thiazol-2-ylmethoxy)-1-(4-(pyrimidin-2-yl)benzyl)-1H-benzo[d]imidazol-2-yl)cyclohexanecarboxylic acid

HRID 2178497Notes

Reaction equation

HRID 2178497 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.[C@@H:36]12[C:45](=O)[O:44][C:42](=[O:43])[C@@H:37]1[CH2:38][CH2:39][CH2:40][CH2:41]2>>[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:45]([C@H:36]3[CH2:41][CH2:40][CH2:39][CH2:38][C@H:37]3[C:42]([OH:44])=[O:43])=[N:33][C:17]=2[CH:18]=1

Participants

4

Reactant 3

HCID 641660Hexahydrophthalic anhydride, cis-HCID 242295594-Pyrimidin-2-ylbenzylamineHCID 904150262-((4-Fluoro-3-nitrophenoxy)methyl)benzo[d]thiazole

Product 1

HCID 86281262racemic cis-2-(5-(Benzo[d]thiazol-2-ylmethoxy)-1-(4-(pyrimidin-2-yl)benzyl)-1H-benzo[d]imidazol-2-yl)cyclohexanecarboxylic acid

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 cis-1,2-cyclohexanedicarboxylic anhydride in step D. MS (ESI): mass calcd. for C33H29N5O3S, 575.69; m/z found, 576.2 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.91-8.78 (d, J=4.9, 2H), 8.50-8.29 (d, J=8.4, 2H), 8.17-7.89 (d, J=8.0, 2H), 7.59-7.57 (d, J=9.2, 1H), 7.57-7.52 (m, 1H), 7.49-7.44 (ddd, J=8.2, 7.2, 1.2, 1H), 7.44-7.43 (d, J=2.4, 1H), 7.39-7.35 (m, 1H), 7.35-7.31 (dd, J=9.1, 2.4, 1H), 7.29-7.26 (d, J=8.5, 2H), 5.95-5.80 (m, 2H), 5.71-5.63 (s, 2H), 3.71-3.62 (dt, J=12.1, 3.9, 1H), 3.04-2.94 (q, J=3.7, 1H), 2.40-2.26 (m, 1H), 2.25-2.14 (m, 1H), 2.11-2.04 (m, 1H), 2.01-1.94 (m, 1H), 1.88-1.73 (m, 1H), 1.73-1.64 (m, 1H), 1.61-1.47 (m, 2H).

Sources & evidence

ORD record
ord-49078a4eb1f54003bd79cc8ba5b25c73
Source dataset
uspto-grants-2015_06
Patent number
US09067917B2

Reaction notes

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