5-Chloro-1H-indole-2-carboxylic acid → HCID 86605145, compound

HRID 1350194Notes

Reaction equation

HRID 1350194 reaction equation
[C:1]([CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH:6]1[NH2:15])([O:3][CH3:4])=[O:2].[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([C:26]([OH:28])=[O:27])=[CH:20]2.ON1C2N=CC=CC=2N=N1.Cl.C(N=C=N)C>O1CCCC1.C(OCC)(=O)C>[C:1]([C@@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C@@H:6]1[NH:15][C:26]([C:21]1[NH:22][C:23]2[C:19]([CH:20]=1)=[CH:18][C:17]([Cl:16])=[CH:25][CH:24]=2)=[O:27])([O:3][CH3:4])=[O:2].[C:1]([C@@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C@H:6]1[NH:15][C:26]([C:21]1[NH:22][C:23]2[C:19]([CH:20]=1)=[CH:18][C:17]([Cl:16])=[CH:25][CH:24]=2)=[O:28])([O:3][CH3:4])=[O:2]

Participants

8

Reactant 4

HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 181649HOAtHCID 582058HCID 582058, compoundHCID 21883477Ethylcarbodiimide hydrochloride

Product 2

HCID 86605145HCID 86605145, compoundHCID 91585624HCID 91585624, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring suspension of 1-carbomethoxy-2-amino-1,2,3,4-tetrahydronaphthalene (cis-trans mixture, 10:1, 150 mg), 5-chloroindole-2-carboxylic acid (143 mg) and 1-hydroxy-7-azabenzotriazole (119 mg) in tetrahydrofuran (20 mL) at room temperature under argon, was added 1-[3-dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (167 mg). After 16 h, the reaction mixture was diluted with ethyl acetate. The organic layer was washed sequentially with 1.0 M aqueous hydrochloric acid solution (20 mL), 1.0 M aqueous sodium hydroxide solution (20 mL) and brine (20 mL), dried over anhydrous magnesium sulfate and evaporated under vacuum to obtain crude product (243 mg) as an oil. The crude product was purified by reverse phase preparative HPLC to obtain cis 1-carbomethoxy-2-(5-chloroindole-2-carbonylamino)-1,2,3,4-tetrahydronaphthalene (167 mg) and trans 1-carbomethoxy-2-(5-chloroindole-2-carbonylamino)-1,2,3,4-tetrahydronaphthalene (14 mg).

Workup

  1. washThe organic layer was washed sequentially with 1.0 M aqueous hydrochloric acid solution (20 mL), 1.0 M aqueous sodium hydroxide solution (20 mL) and brine (20 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated under vacuum
  4. customto obtain crude product (243 mg) as an oil
  5. customThe crude product was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-8cad6a7f29f54bb0bf8c3a2f6d006dc9
Source dataset
uspto-grants-2007_05
Patent number
US07214704B2

Reaction notes

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