Diisopropylethylamine → HCID 57479104, compound

HRID 556490Notes

Reaction equation

HRID 556490 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH2:12][CH3:13])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Br[C:15]1([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=2)[C:23]2[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=2)[NH:17][C:16]1=[O:25].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:24][C:20]1[CH:19]=[C:18]2[C:23]([C:15]([NH:1][C:2]3[C:10]([O:11][CH2:12][CH3:13])=[CH:9][CH:8]=[CH:7][C:3]=3[C:4]([OH:6])=[O:5])([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=3)[C:16](=[O:25])[NH:17]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 19612056HCID 19612056, compoundHCID 575072733-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one

Product 1

HCID 57479104HCID 57479104, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At room temperature, 2-Amino-3-ethoxy-benzoic acid (0.59 g, 3.26 mmol), 3-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (1.21 g, 3.26 mmol) and DIPEA (0.68 ml) were mixed in about 6 ml CH2Cl2. After stirred overnight, the solution was concentrated and the crude product was purified by chromatography to obtain 400 mg solid rac-2-[6-Chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-ylamino]-3-ethoxy-benzoic acid. MS: 471 (M+H)+.

Workup

  1. concentrationthe solution was concentrated
  2. customthe crude product was purified by chromatography

Sources & evidence

ORD record
ord-d089579fc8d84501b8984f503025d8ef
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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