1-(4-Boronophenyl)cyclopropane-1-carboxylic acid → 1-(4'-{4-[1-(2-Chloro-phenyl)-ethoxycarbonylamino]-pyridin-3-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid

HRID 919041Notes

Reaction equation

HRID 919041 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[C:20]1[CH:25]=[CH:24][C:23](OS(C(F)(F)F)(=O)=O)=[CH:22][CH:21]=1)=[O:12])[CH3:9].B([C:37]1[CH:42]=[CH:41][C:40]([C:43]2([C:46]([OH:48])=[O:47])[CH2:45][CH2:44]2)=[CH:39][CH:38]=1)(O)O>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[C:20]1[CH:21]=[CH:22][C:23]([C:37]2[CH:42]=[CH:41][C:40]([C:43]3([C:46]([OH:48])=[O:47])[CH2:45][CH2:44]3)=[CH:39][CH:38]=2)=[CH:24][CH:25]=1)=[O:12])[CH3:9]

Participants

3

Reactant 2

HCID 467396661-(4-Boronophenyl)cyclopropane-1-carboxylic acidHCID 86697086Trifluoro-methanesulfonic acid 4-{4-[1-(2-chloro-phenyl)-ethoxycarbonylamino]-pyridin-3-yl}-phenyl ester

Product 1

HCID 573367851-(4'-{4-[1-(2-Chloro-phenyl)-ethoxycarbonylamino]-pyridin-3-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid

Procedure

Prepared according to the procedure described in Example 1, Step 2, using the following starting materials: trifluoro-methanesulfonic acid 4-{4-[1-(2-chloro-phenyl)-ethoxycarbonylamino]-pyridin-3-yl}-phenyl ester and 1-(4-boronophenyl)cyclopropanecarboxylic acid. After workup the crude material was purified via preparatory HPLC to give the title compound.

Workup

  1. customPrepared
  2. customwas purified via preparatory HPLC

Sources & evidence

ORD record
ord-dcc8cb49b3da443295dde26d5eb7012b
Source dataset
uspto-grants-2016_03
Patent number
US09272990B2

Reaction notes

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