2-Methoxypyrimidine-5-boronic acid → HCID 90415869, compound

HRID 1776785Notes

Reaction equation

HRID 1776785 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:37]=[CH:36][C:15]2[N:16]([CH2:28][C:29]3[CH:34]=[CH:33][C:32](Br)=[CH:31][CH:30]=3)[C:17]([C@H:19]3[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]3[C:25]([OH:27])=[O:26])=[N:18][C:14]=2[CH:13]=1.[CH3:38][O:39][C:40]1[N:45]=[CH:44][C:43](B(O)O)=[CH:42][N:41]=1>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:37]=[CH:36][C:15]2[N:16]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([C:43]4[CH:42]=[N:41][C:40]([O:39][CH3:38])=[N:45][CH:44]=4)=[CH:31][CH:30]=3)[C:17]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]3[C:25]([OH:27])=[O:26])=[N:18][C:14]=2[CH:13]=1

Participants

3

Reactant 2

HCID 27367782-Methoxypyrimidine-5-boronic acidHCID 86281522HCID 86281522, compound

Product 1

HCID 90415869HCID 90415869, compound

Procedure

The title compound was prepared using analogous conditions described in Step A of Example 97 using racemic cis-2-(5-(benzo[d]thiazol-2-ylmethoxy)-1-(4-bromobenzyl)-1H-benzo[d]imidazol-2-yl)cyclohexanecarboxylic acid and (2-methoxypyrimidin-5-yl)boronic acid. MS (ESI): mass calcd. for C34H31N5O4S, 605.72; m/z found, 606.2 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.77-8.72 (s, 2H), 8.01-7.91 (m, 2H), 7.60-7.53 (d, J=8.3, 2H), 7.53-7.48 (m, 1H), 7.45-7.39 (ddd, J=8.2, 7.2, 1.2, 1H), 7.36-7.30 (d, J=2.4, 1H), 7.28-7.23 (d, J=8.3, 2H), 7.23-7.19 (d, J=8.9, 1H), 7.02-6.95 (dd, J=8.8, 2.4, 1H), 5.62-5.47 (m, 4H), 4.03-4.00 (s, 3H), 3.64-3.57 (m, 1H), 2.90-2.81 (dt, J=7.3, 4.1, 1H), 2.45-2.31 (qd, J=7.6, 3.6, 1H), 2.08-2.02 (m, 1H), 1.93-1.81 (m, 2H), 1.81-1.71 (m, 2H), 1.51-1.41 (d, J=14.1, 2H).

Sources & evidence

ORD record
ord-b5d98d0aa1344f9bae541e82ed8f1b8b
Source dataset
uspto-grants-2016_02
Patent number
US09265770B2

Reaction notes

Loading…