Sodium Carbonate → 2-[4-Hydroxy-3-(2-m-tolyl-ethylamino)-benzoylamino]-indane-2-carboxylic acid

HRID 521477Notes

Reaction equation

HRID 521477 reaction equation
C[O:2][C:3]1[CH:23]=[CH:22][C:6]([C:7]([NH:9][C:10]2([C:19]([OH:21])=[O:20])[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11]2)=[O:8])=[CH:5][C:4]=1[NH:24][CH2:25][CH2:26][C:27]1[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=1.B(Br)(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:23]=[CH:22][C:6]([C:7]([NH:9][C:10]2([C:19]([OH:21])=[O:20])[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11]2)=[O:8])=[CH:5][C:4]=1[NH:24][CH2:25][CH2:26][C:27]1[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 44482418HCID 44482418, compound

Product 1

HCID 670766282-[4-Hydroxy-3-(2-m-tolyl-ethylamino)-benzoylamino]-indane-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

10 mg of the compound of example 171 were dissolved in DCM and treated with 200 μl of a 1 M solution of boron tribromide in DCM for 5 h. A 2 M solution of sodium carbonate was added, and the mixture was evaporated in vacuo. The product was purified by preparative RP HPLC (water/ACN gradient).

Workup

  1. customthe mixture was evaporated in vacuo
  2. customThe product was purified by preparative RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-21d84da203e44f1ab70883d05b8e32ca
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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